Water → 4-(4-Hydroxyphenyl)-4-oxobutanoic acid

HRID 355516Notes

Reaction equation

HRID 355516 reaction equation
[O:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:5][CH:4]=1)C.O>II>[OH:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 962WaterHCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

Product 1

HCID 2371304-(4-Hydroxyphenyl)-4-oxobutanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 807IodineSolvent

Conditions

Temperature
140 °C

Procedure

The methoxy derivative, Compound 3.2 (14.54 g, 70 mmol), was dissolved in iodine free hydriodic acid (150 mL) and refluxed at 140° C. for four hours. After the resulting brown solution was cooled to room temperature, water was added and the mixture was neutralized. The aqueous phase was then washed with ether; the organic layers were combined, decolorized, dried and evaporated. The remaining residue was purified by flash silica chromatography to yield a white solid (11.93 g, 88%). 1 H NMR (CDCl3) δ8.20 (d, 2H), 7.02 (d, 2H), 3.32 (t, 2H), 2.88 (d, 2H).

Workup

  1. temperatureAfter the resulting brown solution was cooled to room temperature
  2. washThe aqueous phase was then washed with ether
  3. customdried
  4. customevaporated
  5. customThe remaining residue was purified by flash silica chromatography

Sources & evidence

ORD record
ord-2212cf57977845f58c8a53087ad16ca1
Source dataset
uspto-grants-1998_11
Patent number
US05831073

Reaction notes

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