Ethanol → Hydroxyphenylacetic acid

HRID 653468Notes

Reaction equation

HRID 653468 reaction equation
C([OH:3])C.C([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](P(=O)(O)O)=[O:20])=[CH:14][CH:13]=1)C1C=CC=CC=1.Cl.NO.O.O.O.C([O-])(=O)C.[Na+]>O>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([OH:20])=[O:3])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 20194779HCID 20194779, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 127Hydroxyphenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At first, 1,200 ml of ethanol and 400 ml of water were added to 428 g (1.18 moles) of the compound (d) in a nitrogen atmosphere to prepare a homogeneous solution. Then, 101 g (1.45 moles) of hydroxylamine hydrochloride and 373 g (2.74 moles) of sodium acetate trihydrate were added thereto, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to about 1,000 ml, and extracted with ethyl ether (3×300 ml). The ethyl ether layer was washed successively with an aqueous 5% sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution (each 2×100 ml), and dried over anhydrous sodium sulfate. The solvent was removed therefrom under reduced pressure to obtain 441 g of the compound (a) as an orange oily substance (99.1%).

Workup

  1. customto prepare a homogeneous solution
  2. concentrationThe reaction mixture was concentrated under reduced pressure to about 1,000 ml
  3. extractionextracted with ethyl ether (3×300 ml)
  4. washThe ethyl ether layer was washed successively with an aqueous 5% sodium hydrogen carbonate solution
  5. dry with materialan aqueous saturated sodium chloride solution (each 2×100 ml), and dried over anhydrous sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-a21b8e0198a44b669804d046850d16f7
Source dataset
uspto-grants-1987_06
Patent number
US04677125

Reaction notes

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