Acetic Anhydride → 2-[2-Hydroxy-3-(o-tolyloxy)phenyl]glycine

HRID 1164034Notes

Reaction equation

HRID 1164034 reaction equation
C[O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:17]([C:19]([OH:21])=[O:20])[NH2:18].C(OC(=O)C)(=O)C.I.[OH-].[Na+]>O>[OH:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:17]([C:19]([OH:21])=[O:20])[NH2:18]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 130666872-[2-Methoxy-3-(o-tolyloxy)phenyl]glycine

Product 1

HCID 130666882-[2-Hydroxy-3-(o-tolyloxy)phenyl]glycineYield 7,040.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[2-Methoxy-3-(o-tolyloxy)phenyl]glycine (22.4 g) was added to a mixture of acetic anhydride (75 ml) and hydriodic acid (55-58%, 150 ml), and the mixture was refluxed under heating for 9 hours. The reaction mixture was poured into water (1 l) and adjusted to pH 12 with 20% aqueous sodium hydroxide. The solution was washed with diethyl ether and adjusted to pH 6.0 with conc. hydrochloric acid. The precipitating crystals were collected by filtration washed with water and dried to give 2-[2-hydroxy-3-(o-tolyloxy)phenyl]glycine (1500 g). mp 170°-173° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 9 hours
  3. washThe solution was washed with diethyl ether
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-29b5d32953ad4b04bc3e77a13855c336
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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