Hydrochloric Acid → 4-(Hydroxymethyl)phenylacetic acid

HRID 977887Notes

Reaction equation

HRID 977887 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].C([O-])(=[O:17])C.[Na+].Cl>O>[OH:17][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 32834984-(Hydroxymethyl)phenylacetic acidYield 55.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 9.00 g (39.3 mmol) of p-bromomethylphenylacetic acid, 3.14 g (78.6 mmol) of sodium hydroxide and 3.54 g (43.2 mmol) of sodium acetate in 40 ml of water was stirred for 4 hours at 100° C. At the end of this time, it was cooled to room temperature and then acidified with 2N aqueous hydrochloric acid. It was then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from a mixture of ethyl acetate and methylene chloride to give 3.60 g (yield 55%) of the title compound, melting at 136°-137° C.

Workup

  1. extractionIt was then extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was recrystallized from a mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-6d823bd6f5da43928f3628c2e93c8122
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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