Potassium Hydroxide → HCID 10621058, compound

HRID 322856Notes

Reaction equation

HRID 322856 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]1[CH:27]=[C:26]([C:28]([O:30]CC)=[O:29])[O:25][N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]1[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[O:25][N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10765021HCID 10765021, compound

Product 1

HCID 10621058HCID 10621058, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 3-(2,4-dibenzyloxyphenyl)isoxazole-5-carboxylate (2.2 g) in hot methanol (100 mL) is treated with 10% aqueous potassium hydroxide solution (10 mL w/v) and the mixture is heated to reflux for 2 hours. The reaction mixture is evaporated to low bulk, stirred with 1 N hydrochloric acid (50 mL) for 15 minutes and filtered. The resulting solid is washed with water, dried and crystallised from ethyl acetate to give 3-(2,4-dibenzyloxyphenyl)isoxazole-5-carboxylic acid (1 g), in the form of a white solid, m.p. 192-193° C. [Elemental analysis:- C,71.7; H,4.67; N,3.34%. Calculated:- C,71.8; H,4.77; N,3.49%].

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 2 hours
  3. customThe reaction mixture is evaporated to low bulk
  4. filtrationfiltered
  5. washThe resulting solid is washed with water
  6. customdried
  7. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-28c86d86ea034610adccb8175d7ff336
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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