Methanol → 2',3'-Dihydroxyacetophenone

HRID 1603922Notes

Reaction equation

HRID 1603922 reaction equation
C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][CH:6]=[CH:5][C:4]=1[C:11](=[O:13])[CH3:12].B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 124074131-(2,3-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 64291102',3'-DihydroxyacetophenoneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2',3'-dimethoxyacetophenone (4.85 g, 26.9 mmol) in dichloromethane (100 ml) was added at -70° C. with a 1M boron tribromide solution in dichloromethane (68 ml). The mixture was left to cool, keeping stirring for 2.5 hours at room temperature, then added with methanol (70 ml), left under stirring for 1 h, thereafter evaporated to dryness. The residue was dissolved in ethyl acetate (250 ml), washed with 2% NaHCO3 (1×30 ml), dried and the solvent was evaporated off, to obtain a crude which was purified by crystallization in methanol, thereby obtaining 3.10 g of the title compound as a yellow solid (76% yield).

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. waitleft
  4. stirringunder stirring for 1 h
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in ethyl acetate (250 ml)
  7. washwashed with 2% NaHCO3 (1×30 ml)
  8. customdried
  9. customthe solvent was evaporated off
  10. customto obtain a crude which
  11. customwas purified by crystallization in methanol

Sources & evidence

ORD record
ord-2a1aa87c93d743f9a362f54196019a30
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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