Diazomethane → HCID 21413830, compound

HRID 268500Notes

Reaction equation

HRID 268500 reaction equation
[N+](=[CH2:3])=[N-].[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1>CCOCC>[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:3])=[O:21])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 21413792HCID 21413792, compound

Product 1

HCID 21413830HCID 21413830, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of diazomethane in 75 ml. of ether is added, portionwise, as a solid, 1.0 gm. of 4-(benzoxazol-2-yl)phenylacetic acid. Nitrogen is evolved and after 1 hour the excess diazomethane is consumed by adding acetic acid. The reaction mixture is filtered and the filtrate concentrated to give a yellow solid. Recrystallization from methanol gives methyl 4-(benzoxazol-2-yl)phenylacetate, m.p. 109°-112°C.

Workup

  1. customthe excess diazomethane is consumed
  2. additionby adding acetic acid
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate concentrated
  5. customto give a yellow solid
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-a8c4acea66c94ab1ba1fa725658f1d59
Source dataset
uspto-grants-1976_03
Patent number
US03947582

Reaction notes

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