Water → HCID 19898999, compound

HRID 1196667Notes

Reaction equation

HRID 1196667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:19]([O:21]C)=[O:20])[CH2:18][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:19]([OH:21])=[O:20])[CH2:18][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 19899110HCID 19899110, compound

Product 1

HCID 19898999HCID 19898999, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.4 g (0.039 mol) of methyl 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-8-carboxylate were stirred for 18 hours in 10 ml of methanol, 0.5 g of potassium hydroxide and 2 ml of water. The methanol was removed by evaporation and the residual gum was dissolved in water. Acidification with a few drops of concentrated hydrochloric acid gave a white granular precipitate which was filtered off, washed with water and dried. After crystallization from glacial acetic acid, there were obtained 1.9 g of 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-8-carboxylic acid of melting point 215° C.

Workup

  1. customThe methanol was removed by evaporation
  2. dissolutionthe residual gum was dissolved in water
  3. customAcidification with a few drops of concentrated hydrochloric acid gave a white granular precipitate which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried
  7. customAfter crystallization from glacial acetic acid

Sources & evidence

ORD record
ord-4c8d0fbf0965416cbaa0ef3225aa8628
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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