Ethanol → 4-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl ester

HRID 2042624Notes

Reaction equation

HRID 2042624 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.[CH2:16](O)[CH3:17]>Br.C(O)(=O)C>[CH2:16]([O:14][C:12](=[O:13])[CH2:11][CH2:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1)=[O:15])[CH3:17]

Participants

5

Reactant 2

HCID 702EthanolHCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

Product 1

HCID 114359904-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

In a 1 L round bottom flask, 4-(4-methoxyphenyl)-4-oxo-butyric acid (25 g, 106 mmol) in 48% HBr (125 mL) and acetic acid (250 mL) was heated to reflux 18 h. The reaction was cooled slightly and ethanol (250 mL) was added. The solvent was concentrated under vacuum. Additional ethanol (100 mL) was added and solvent concentrated under vacuum again. The resulting oil was crystallized from ethyl acetate/hexanes to produce 8.65 g (37%). MS m/z=223 (M+H).

Workup

  1. temperatureto reflux 18 h
  2. temperatureThe reaction was cooled slightly
  3. concentrationThe solvent was concentrated under vacuum
  4. additionAdditional ethanol (100 mL) was added
  5. concentrationsolvent concentrated under vacuum again
  6. customThe resulting oil was crystallized from ethyl acetate/hexanes
  7. customto produce 8.65 g (37%)

Sources & evidence

ORD record
ord-81aa97546f8345bc85827121bd245ad4
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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