Glycolic Acid → ({[(4-Nitrophenyl)methoxy]carbonyl}oxy)acetic acid

HRID 1252200Notes

Reaction equation

HRID 1252200 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N(CC)CC)C.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15]>O1CCCC1.C(OCC)(=O)C>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:16][C:14]([O:3][CH2:2][C:1]([OH:5])=[O:4])=[O:15])=[CH:23][CH:22]=1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 757Glycolic AcidHCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 20140862({[(4-Nitrophenyl)methoxy]carbonyl}oxy)acetic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of glycolic acid (760 mg) and triethylamine (1.1 g) in tetrahydrofuran (20 ml) was added p-nitrobenzyl chloroformate (2.26 g) with ice-cooling and the resulting mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, washed successively with diluted hydrochloric acid and water, dried over anhydrous sodium sulfate and evaporated to give p-nitrobenzyloxycarbonyloxyacetic acid.

Workup

  1. temperaturecooling
  2. washwashed successively with diluted hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c7ea17500e684e169b0dbf7ccd6a4dae
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

Loading…