Diazomethane → 2-Isopropoxyimino-2-phenylacetic acid

HRID 328456Notes

Reaction equation

HRID 328456 reaction equation
[C:1]1([C:7](=O)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH:13]([O:16][NH2:17])([CH3:15])[CH3:14].[OH-].[Na+].[N+](=C)=[N-]>O.C(O)C>[CH:13]([O:16][N:17]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([OH:10])=[O:9])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 9550DiazomethaneHCID 11915Phenylglyoxylic AcidHCID 14798Sodium Hydroxide2×HCID 12696235O-(propan-2-yl)hydroxylamine hydrochloride

Product 1

HCID 542830792-Isopropoxyimino-2-phenylacetic acidYield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of phenylglyoxylic acid (3.0 g.), isopropoxyamine hydrochloride (2.5 g.), ethanol (100 ml) and water (50 ml) was stirred and adjusted to pH 4.5 to 5 with sodium hydroxide solution (2N). The solution was stirred for 5 hr. maintaining the pH at 4.5-5 with further additions of sodium hydroxide solution. The ethanol was removed by evaporation, the aqueous residue acidified and the product collected by extraction with ethyl acetate. Evaporation of the ethyl acetate gave a brown oil (4.2 g.). that was esterified conventionally with diazomethane to give a mixture of the syn and anti methyl esters of the title compound as an oil (4.04 g.).

Workup

  1. stirringThe solution was stirred for 5 hr
  2. customThe ethanol was removed by evaporation
  3. customthe product collected by extraction with ethyl acetate
  4. customEvaporation of the ethyl acetate
  5. customgave a brown oil (4.2 g.)
  6. customto give

Sources & evidence

ORD record
ord-a629001ca31647a0bd465725c63cd119
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Reaction notes

Loading…