2-tert-Butyl-4-hydroxyanisole → 2-tert-Butyl-4-hydroxyanisole

HRID 2417729Notes

Reaction equation

HRID 2417729 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([OH:19])=[CH:17][C:16]=1[C:22]([CH3:25])([CH3:24])[CH3:23]>CO>[C:1]([C:5]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:2])[CH3:3].[C:22]([C:16]1[CH:17]=[C:18]([OH:19])[CH:20]=[CH:21][C:15]=1[O:14][CH3:13])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 69322-tert-Butyl-4-hydroxyanisoleHCID 16043Tert-Butylhydroquinone

Product 2

HCID 69322-tert-Butyl-4-hydroxyanisoleHCID 8456Butylated Hydroxyanisole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g of tert-butyl-hydroquinone, 40 cm3 of methanol and 1.0 g of cupric chloride are fed into the autoclave. The autoclave is purged with nitrogen and kept at 105° C. for 2.5 hours. On termination of the reaction, mixture analysis indicates the formation of 4.4 g of tert-butyl-hydroquinone monomethyl ether (BHA) (conversion 100%, selectivity 82%). The two BHA isomers (3-tert-butyl-4-hydroxyanisole and 2-tert-butyl-4-hydroxyanisole) are formed in a weight ratio of 99:1.

Workup

  1. customThe autoclave is purged with nitrogen
  2. customOn termination of the reaction, mixture analysis

Sources & evidence

ORD record
ord-0a1acd4bef8c441bb685e10cda75f930
Source dataset
uspto-grants-1984_09
Patent number
US04469897

Reaction notes

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