Hydrochloric Acid → 1-(4-Hydroxyphenyl)-2-methoxyethan-1-one

HRID 2099927Notes

Reaction equation

HRID 2099927 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12][O-:13].[Na+].Cl>CO>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][O:13][CH3:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 10942334Sodium Methoxide

Product 1

HCID 30156141-(4-Hydroxyphenyl)-2-methoxyethan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3.0 g of 2-bromo-1-(4-hydroxy-phenyl)-ethanone in 25 ml of methanol are added dropwise in the course of 10 minutes to a solution of 7.5 g of sodium methanolate in 80 ml of methanol. Stirring is then carried out at 60° C. for 45 minutes. The reaction mixture is cooled, poured into dilute hydrochloric acid and extracted with ethyl acetate. After concentration of the organic phases and crystallisation from diethyl ether, 1-(4-hydroxy-phenyl)-2-methoxyethanone is obtained. 1H-NMR (CDCl3) 300 MHz: 3.50 (s, 3H), 4.70 (s, 2H), 6.62 (s, 1H), 6.91 (d, 2H), 7.89 (d, 2H)

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. customAfter concentration of the organic phases and crystallisation from diethyl ether

Sources & evidence

ORD record
ord-09684e6c5933432a8d839d38224fb707
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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