Hydrochloric Acid → HCID 131711179, compound

HRID 2419238Notes

Reaction equation

HRID 2419238 reaction equation
Cl.[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][CH2:10][C:11]([NH:13][CH:14](O)[C:15]([OH:17])=[O:16])=[O:12]>C(O)(=O)C>[Cl:9][CH2:10][C:11]([N:13]([C:5]1[CH:6]=[CH:7][C:2]([OH:8])=[CH:3][CH:4]=1)[CH2:14][C:15]([OH:17])=[O:16])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 996PhenolHCID 23257102(2-Chloroacetamido)(hydroxy)acetic acid

Product 1

HCID 131711179HCID 131711179, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

18 g of gaseous hydrochloric acid at 5° C are dissolved in a solution of 94 g (1 mole) of phenol and 83.8 g (0.5 mole) of chloracetamidoglycolic acid in 120 g of glacial acetic acid. After 8 hours at this temperature and then 16 hours at ambient temperature, the hydrochloric and acetic acids are distilled off at 25 mm of mercury, then the excess phenol at 2 mm of mercury at a temperature below 50° C, 200 ml of nitromethane are added, it is filtered, washed with ethyl ether and dried. 64 g of product are obtained (yield 53% with respect to the chloracetamidoglycolic acid). The product recrystallised in water melts at 187° C.

Workup

  1. distillation16 hours at ambient temperature, the hydrochloric and acetic acids are distilled off at 25 mm of mercury
  2. additionthe excess phenol at 2 mm of mercury at a temperature below 50° C, 200 ml of nitromethane are added
  3. filtrationit is filtered
  4. washwashed with ethyl ether
  5. customdried

Sources & evidence

ORD record
ord-50df6169d2ed4759985eccd8d3aae910
Source dataset
uspto-grants-1978_08
Patent number
US04105690

Reaction notes

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