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

HRID 2396568Notes

Reaction equation

HRID 2396568 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%). NMR (CDCl3) δ 8.20 (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-d1d375fbf48e4505a6d2404c665d5ee7
Source dataset
uspto-grants-1996_02
Patent number
US05493012

Reaction notes

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