Hydrogen Bromide → 4,5-Dimethylbenzene-1,2-diol

HRID 1706690Notes

Reaction equation

HRID 1706690 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:11]C)[C:5]([O:9]C)=[CH:6][C:7]=1[CH3:8].Br>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:6][C:7]=1[CH3:8])[OH:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 187953521,2-Dimethoxy-4,5-dimethylbenzene

Product 1

HCID 127302874,5-Dimethylbenzene-1,2-diol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

53 g of 4,5-dimethylveratrol (prepared by the method of Bruce, et al., J. Chem. Soc., 1956, 3824-29) was mixed with 200 ml of 48% hydrobromic acid. The mixture was stirred at reflux temperature, in a nitrogen atmosphere, for 4.5 hours. The crude mixture was heated with 200 ml of toluene. The toluene phase was separated and cooled, to give 4,5-dimethylcatechol (6A), as a solid, mp: 86°-87° C.

Workup

  1. temperatureat reflux temperature
  2. customThe toluene phase was separated
  3. temperaturecooled

Sources & evidence

ORD record
ord-142956469dcc4d00b6e6b6945384307c
Source dataset
uspto-grants-1980_06
Patent number
US04208424

Reaction notes

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