Acetic Acid → N-(4-Hydroxyphenyl)glycine

HRID 2419239Notes

Reaction equation

HRID 2419239 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH3:9].[C:10]([OH:13])(=[O:12])[CH3:11]>>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([NH:9][CH2:11][C:10]([OH:13])=[O:12])=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 962WaterHCID 996Phenol

Product 1

HCID 67149N-(4-Hydroxyphenyl)glycine

Conditions

Temperature
20 °C

Procedure

To a solution in 120 g of acetic acid and 113.5 g of 95% sulfuric acid, of acetamidoglycolic acid obtained from 1 mole of glyoxylic acid, are added in 2 hours, 376 g (4 moles) of phenol in solution in 120 g of acetic acid, keeping the temperature below 5° C, then allowing to stand for 16 hours at room temperature. 1 liter of water is then added and it is boiled under reflux for 4 hours to hydrolyse the N-acyl derivative. After cooling to 20° C, the pH is brought to 1.5 with ammonia, the excess of phenol is extracted with 3 times 200 ml of butyl acetate. The aqueous phase concentrated at 1200 g is brought to pH 5.5 with ammonia, the precipitate formed is filtered, washed with water and dried.

Workup

  1. additionare added in 2 hours
  2. customthe temperature below 5° C
  3. temperatureunder reflux for 4 hours
  4. extractionthe excess of phenol is extracted with 3 times 200 ml of butyl acetate
  5. concentrationThe aqueous phase concentrated at 1200 g
  6. customthe precipitate formed
  7. filtrationis filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-5784112753e04b049446368933104513
Source dataset
uspto-grants-1978_08
Patent number
US04105690

Reaction notes

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