Benzyl Alcohol → Toluene

HRID 236874Notes

Reaction equation

HRID 236874 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)C1C=CC=CC=1>[Co]>[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1([CH3:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 60542-Phenylethanol2×HCID 7501Styrene

Product 2

HCID 1140TolueneYield 50%HCID 60542-PhenylethanolYield 25%

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

It has long been desirable to prepare β-phenylethyl alcohol in a low cost process. This material is a valuable intermediate in the preparation of fragrances and of styrene, a commercial chemical with widely varying uses. In the past, it has been proposed that β-phenylethyl alcohol be prepared from benzyl alcohol. For example, the reaction has been described by Wender, I. et al., J. Am. Chem. Soc. 71 (1949), pages 4160-4161 in the presence of a cobalt catalyst. This early work is summarized by Orchin in Advances in Catalysis, Vol. V (1953), pages 393-414. This author reports that, at 185° C., a 50-60% yield of toluene and a 25-35% yield of β-phenylethanol is obtained. Other workers have experimented with this reaction, particularly Y. B. Kryukov et al., Neftekhimiya, 1970, 10 (1), at page 83. Here, a vapor phase reaction is described over an iron, alumina, vanadium and potassium catalyst at 450° C. and 50 atmospheres pressure. Unfortunately, in this latter reaction extremely low selectivities to the β-phenylethanol were obtained.

Workup

  1. customin the preparation of fragrances
  2. customat 185° C.

Sources & evidence

ORD record
ord-2139fe2f687345acba2122cb0131ab13
Source dataset
uspto-grants-1979_06
Patent number
US04158100

Reaction notes

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