Benzoic acid from benzyl alcohol

We have also found that BTMA Br3 can be used as a reagent for the oxidation of benzyl alcohols to benzoic acids. That is, the reaction of benzyl alcohols with 2-equiv. of BTMA Br3 in an aq. alkaline solution at room temperature or at 70°C afforded benzoic acids in good yields. Thus, we could selectively obtain the oxidation products, benzaldehydes and benzoic acids, from benzyl alcohols by using a stoichiometric amount of BTMA Br3 (Fig. 24) (ref. 32). 

Flowchart for separation of benzoic acid from benzyl alcohol. 

Oxidation Products.—Ai-omatic alcohols possessing the group -CHoOH may readih be oxidized to the corresponding acid. Example Benzoic acid from benzyl alcohol. The method is similar to that to be outlined later in this chapter for the oxidation of side-chains of aromatic hydrocarbons except that the reaction is more rapid and the yields are higher. 

CANNIZZARO S REACTION. BENZOIC ACID AND BENZYL ALCOHOL FROM BENZALDEHYDE 1... 

Benzyl benzoate is rapidly absorbed from the stomach. It is rapidly hydrolyzed to benzoic acid and benzyl alcohol, which is subsequently hydrolyzed to benzoic acid. Benzoic acid is conjugated with glycine to give benzoylglycine or hippuric acid and with glucuronic acid to give benzoylglucuronic acid. The... 

Example Benzoic Acid and Benzyl Alcohol from Benzaldehyde1... 

Figure 13.1 shows a flowchart for the separation of benzoic acid, a water-insoluble carboxylic acid, from benzyl alcohol, a water-insoluble nonacidic compound. First, we dissolve the mixture of benzoic acid and benzyl alcohol in diethyl ether. Next, we shake the ether solution with aqueous NaOH to convert benzoic acid to its water-soluble sodium salt. Then we separate the ether from the aqueous phase. Distillation of the ether solution yields first diethyl ether (bp 35 °C) and then benzyl alcohol (bp 205 °C). When we acidify the aqueous solution with HCl, benzoic acid precipitates as a water-insoluble solid (mp 122 °C) and is recovered by filtration. The ability to separate compounds based on their acid-base properties is very important in laboratory and industrial chemistiy. ... 

Benzoic acids and benzyl alcohols (D 22.2.5) Diketides derived from cinnamic acids (D 22.3.1) Triketides derived from cinnamic acids (D 22.3.2) Stilbenes and flavonoids (D 22.3.3)... 

Purpose. This experiment illustrates the simultaneous oxidation and reduction of an aromatic aldehyde to form the corresponding benzoic acid and benzyl alcohol. The experiment further demonstrates the techniques for separation of a carboxylic acid from a neutral alcohol. For a detailed discussion of this extraction procedure, see Experiment [4C]. 

How would you make the following compounds from A-benzylbenzamide a. dibenzylamine b. benzoic acid c. benzyl alcohol... 

In F, benzyl alcohol is the hydrogen-rich product from hydride transfer to benzaldehyde in the Cannizzaro reaction the hydrogen-deficient species is benzoic acid. Hydride transfer to the carbonium ion derived from benzyl alcohol also results in the formation of toluene, an even more reduced species. As shov n in Equations 11 and 12, these Cannizzaro-like transformations are essentially redox type, at least in respect to hydrogen balance. 

This reaction could also afford the heptaldehyde self-condensation product, some benzyl alcohol and benzoic acid (from the Cannizzaro reaction) as byproducts authors reported that a higher temperature favours the jasminaldehyde formation. By slowly adding heptaldehyde, to keep its concentration low, a 99%... 

In the top section of the distillation, the acetal is formed from the light benzaldehyde and benzyl alcohol. The high boiling acetal falls down to the bottom section and is decomposed by reaction with benzoic acid into benzyl benzoate, benzaldehyde and benzyl alcohol. This is probably also one of the reasons why it is so difficult to remove all traces of benzyl alcohol and benzaldehyde from benzoic acid by distillation. 

In the past benzal and benzyl chlorides were co-produced for the manufacture of benzaldehyde and benzyl alcohol, but today the vast majority of the benzaldehyde produced from benzal chloride is that which is made from recovered (by-product) material. For an historical article regarding the chlorination of toluene and the subsequent production of benzaldehyde, benzyl alcohol, and benzoic acid, see reference 4. 

The main oxidation product from dibenzyl ether is benzaldehyde (up to 80% yield) with smaller amounts of benzyl alcohol and benzoic acid. The rates of oxidation are only slightly affected by major stereochemical changes, and it is considered that an outer-sphere oxidation of the ether is followed by radical breakdown, viz. 

The aqueous alkaline liquid (from which the benzyl alcohol was removed with ether) is acidified with hydrochloric acid. Benzoic acid is precipitated and, when cold, is filtered off with suction. It is recrystallised from boiling water without previous washing. Melting point 121°. Yield 9-10 g. 

Photolytic. A n-hexane solution containing /n-xylene and spread as a thin film (4 mm) on cold water (10 °C) was irradiated by a mercury medium pressure lamp. In 3 h, 18.5% of the p-xylene photooxidized into p-methylbenzaldehyde, p-benzyl alcohol, p-benzoic acid, and p-methylacetophenone (Moza and Feicht, 1989). Glyoxal and methylglyoxal were produced from the photooxidation of p-xylene by OH radicals in air at 25 °C (Tuazon et al., 1986a). The rate constant for the reaction of p-xylene and OH radicals at room temperature was 1.22 x lO " cmVmolecule-sec (Hansen et al., 1975). A rate constant of 7.45 x 10 L/molecule-sec was reported for the reaction of p-xylene with OH radicals in the gas phase (Darnall et al, 1976). Similarly, a room temperature rate constant of 1.41 x 10 " cm /molecule-sec was reported for the vapor-phase reaction of p-xylene with OH radicals (Atkinson, 1985). At 25 °C, a rate constant of 1.29 x lO " cmVmolecule-sec was reported for the same reaction (Ohta and Ohyama, 1985). 

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