Hydrochloric Acid → 4'-Hydroxy-3'-methoxy-2-bromoisobutyrophenone

HRID 2395724Notes

Reaction equation

HRID 2395724 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:16])[C:12]([Br:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9]C.[Br-].[Al+3].[Br-].[Br-].Cl>C1(C)C=CC=CC=1>[OH:9][C:8]1[CH:7]=[CH:6][C:5]([C:11](=[O:16])[C:12]([Br:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 166749BromhydrolHCID 132202043',4'-Dimethoxy-2-bromoisobutyrophenone

Product 1

HCID 189903364'-Hydroxy-3'-methoxy-2-bromoisobutyrophenoneYield 91.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3',4'-dimethoxy-2-bromoisobutyrophenone (11.5 g) and aluminium bromide (21.8 g) in toluene (220 ml) was refluxed for 15 min. After cooling the reaction mixture was poured into ice (300 g) and 1N hydrochloric acid (200 ml). The organic phase was separated and dried over Na2SO4. The solvent was evaporated in vacuo yielding a pale yellow oil (10.0 g).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d84e182d1db44fcf882d090cd713b4de
Source dataset
uspto-grants-1996_02
Patent number
US05489614

Reaction notes

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