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(iii) Metabolism of benzyl alcohol, benzoic acid, and related esters

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Carboxylic acid Ester Esterification: Preparation of Methyl Benzoate Narattapat Watcharapariyapat Mahidol University International College Narattapat@student.
nitration of methyl benzoate (electrophilic aromatic substituition.

To synthesis triphenylmethanol from Grignard reaction.Methyl 4-(trimethylsilylethynyl)benzoate.

The benzyl derivatives are rapidly absorbed through the gut, metabolized primarily in the liver, and excreted in the urine as glycine conjugates of benzoic acid derivatives (Davison, 1971; Abdo et al., 1985; Temellini, 1993), as discussed by the Committee at its forty-sixth meeting, when it evaluated benzyl alcohol (No. 25), benzyl acetate (No.23), benzaldehyde (No. 22), and benzoic acid (No. 850) (Annex 1, reference ). After absorption, benzyl derivatives are metabolized and excreted within 24 h as polar metabolites, mainly as urinary hippuric acid (Table 3).

Experiment 5 - Nitration of Methyl Benzoate

Quantitative data on natural occurrence were available for 10 substances in the group (CIVO-TNO, 2000), and consumption ratios were calculated (Stofberg & Kirschman, 1985; Stofberg & Grundschober, 1987). The consumption ratio for the substance for which the reported annual volume of use in Europe is highest (benzyl alcohol, No. 25) is 0.06, and that for the substance with the highest reported annual volume in the USA (benzaldehyde, No. 22) is 0.2. The consumption ratios for benzyl formate (No. 841), benzyl benzoate (No. 24), and methyl benzoate (No. 851) are

Benzyl esters and acetals are hydrolysed to benzyl alcohol and carboxylic acids and to benzaldehyde and alcohols, respectively. Benzyl alcohol and benzaldehyde are rapidly oxidized to benzoic acid, while benzoate esters are hydrolysed to benzoic acid and alcohols. The benzoic acid derivatives are excreted primarily as glycine conjugates. Benzoic acid is readily conjugated with glycine, primarily in the liver (see Figure 1). After high doses, formation of the glycine conjugate is limited by the concentration of glycine. When glycine is depleted, free benzoic acid may sequester acetyl coenzyme A or be excreted unchanged or as the glucuronic acid conjugate (Diack & Lewis, 1928; Bray et al., 1951; Williams, 1959; Abdo & Wenk, 1995; Abdo et al., 1998). The metabolism, including hydrolysis, of flavouring agents that were not reviewed by the Committee at its forty-sixth meeting is summarized below.

Nitration of Methyl Benzoate | Aromaticity | Organic …

Benzyl and benzoate esters in the group of benzyl derivatives are anticipated to be hydrolysed rapidly to yield the corresponding alcohols and carboxylic acids, as shown in several studies and . Benzyl acetate (No. 23) is hydrolysed rapidly, both and (Heymann, 1980; Yuan et al., 1995; Annex 1, reference ).

A subgroup of benzyl derivatives comprising benzyl alcohol (No. 25), benzaldehyde (No. 22), benzyl acetate (No. 23), and benzoic acid (No. 850) and salts was the subject of a recent comprehensive review and safety evaluation by the Committee (Annex 1, references and ). The review and evaluation contain detailed descriptions of most of the studies on specific benzyl derivatives. The following sections give only summaries of the results of studies described in detail in that review. Other relevant studies, including studies on other benzyl derivatives not discussed in the review, are described in detail.

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Nitration of Methyl Benzoate by Jamie Stewart on Prezi

This monograph summarizes the key data relevant to the safety evaluation of 37 derivatives of benzyl alcohol, benzaldehyde, or benzoic acid (Table 1). All members of this group are aromatic primary alcohols, aldehydes, carboxylic acids, or their corresponding esters or acetals. The structural features common to this group of substances include an oxygenated functional group bonded directly to a benzene ring which may be ring-substituted with alkyl substituents. The group contains the parent saturated alcohol, benzyl alcohol (No. 25), and related benzyl esters (Nos 23–24 and 841–849); the corresponding aldehyde, benzaldehyde (No. 22), and related acetals (Nos 837–840); and the corresponding parent carboxylic acid, benzoic acid (No. 850), and related benzoate esters (Nos 851–862). The group also includes seven additional structurally related benzyl derivatives (Nos 863–869) containing ring alkyl substituents.

24-4-2014 · Nitration of Methyl Benzoate Mechanism ..

Methyl benzoate (No. 851), ethyl benzoate (No. 852), propyl benzoate (No. 853) and benzyl benzoate (No. 24) are all hydrolysed to benzoic acid and the corresponding alcohol after incubation with human plasma, diluted to 80% with phosphate buffer at pH 7.4 and 37 °C. The half-times were was 108 min for methyl benzoate, 210 min for ethyl benzoate, 46 min for propyl benzoate, and 19 min for benzyl benzoate (Nielsen & Bundgaard, 1987).


The reaction is then poured over ice.
Procedure con't
The product is isolated through vacuum filtration
Product was washed with cold distilled water
Product was washed again with portions of methanol that totaled 15ml
.698 Crude product was collected
Recrystallization was performed with determined volume of methanol needed per mass of crude product and density of methanol
Methanol amount was added to beaker of crude product
The beaker was placed in a larger beaker of water that was heated to 80˚C
Product was swirled until melted
Solution was then allowed to cool slowly until recrystallization
Crystals were collected through vacuum filtration and rinsed with methanol
Purified final product recovered was .186g
mp 78˚C
Results Con't
IR Spectrum
NMR Spectrum
Results Con't
Product yield was low, but expected product was recovered based on the testing:
Melting Point was exact as standard
IR showed functional groups
NMR showed the benzene and carboxymethoxy group
TLC showed polar Methyl-M-Nitrobenzoate

24/04/2014 · Nitration of Methyl Benzoate Mechanism ..

The metabolism of benzyl alcohol (No. 25), benzyl acetate (No. 23), benzaldehyde (No. 22), and benzoic acid (No. 850) was described comprehensively by the Committee at its forty-sixth meeting (Annex 1, reference ).

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