Benzyl Alcohol → Diphenylmethane

HRID 1651850Notes

Reaction equation

HRID 1651850 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1C=CC=CC=1>[C:2]1([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 244Benzyl Alcohol3×

Product 3

HCID 244Benzyl AlcoholHCID 7580DiphenylmethaneYield 16%HCID 10934161Benzene, 1,2-bis(phenylmethyl)-Yield 4.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzylation of some aromatics with benzyl alcohol in the presence of askanite is known from J. General Chemistry of the USSR (English translation of Z. obsz. Zhim.) 20 (1950), 2249 (page 2168 in the original). This procedure is carried out at 90° C. and at 10% by weight of askanite, relative to the benzyl alcohol. If 200 g of benzyl alcohol and 200 g of benzene (molar ratio 1:1.38) are used, about 16% of diphenylmethane and 4.6% of dibenzyl-benzene, all relative to benzyl alcohol, are obtained; the non-distillable residue is larger than the total amount of diphenylmethane and dibenzyl-benzene. In the benzylation of toluene under the same conditions 10.8% of dibenzyl-toluene, both relative to benzyl alcohol, are obtained.

Workup

  1. customis carried out at 90° C. and at 10% by weight

Sources & evidence

ORD record
ord-15024b90f8114b65ab7e9dc0c06b1a35
Source dataset
uspto-grants-1990_05
Patent number
US04929784

Reaction notes

Loading…