Potassium Hydroxide → HCID 19899088, compound

HRID 1196679Notes

Reaction equation

HRID 1196679 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH2:14][CH2:15][CH:16]([C:19]([O:21]C)=[O:20])[CH2:17][CH2:18][C:12]=3[O:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]3[CH2:14][CH2:15][CH:16]([C:19]([OH:21])=[O:20])[CH2:17][CH2:18][C:12]=3[O:11][N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19899021HCID 19899021, compound

Product 1

HCID 19899088HCID 19899088, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

1.7 g (0.00565 mol) of methyl 5,6,7,8-tetrahydro-3-(4-methoxyphenyl)-4H-cyclohept[d]isoxazole-6-carboxylate were dissolved in 20 ml of methanol. 1 g of potassium hydroxide in 3 ml of water was added and the mixture was stirred at 20° C. for 66 hours. The methanol was removed by evaporation and an excess of water was added. The mixture was acidified with dilute hydrochloric acid and the resulting precipitate was filtered off, washed with water and dried. Crystallization from ethyl acetate/hexane gave 1.1 g of 5,6,7,8-tetrahydro-3-(4-methoxyphenyl)-4H-cyclohept[d]isoxazole-6-carboxylic acid of melting point 147°-148° C.

Workup

  1. customThe methanol was removed by evaporation
  2. additionan excess of water was added
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c0f0e318090242f08ebb969629c7694c
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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