Water → HCID 19899117, compound

HRID 1196672Notes

Reaction equation

HRID 1196672 reaction equation
ClC1C=CC(C2C3CCC(C(OC)=O)CCCC=3ON=2)=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:34]3[CH2:35][CH2:36][CH2:37][CH:38]([C:41]([O:43]C)=[O:42])[CH2:39][CH2:40][C:33]=3[O:32][N:31]=2)=[CH:26][CH:25]=1.[OH-].[K+].O>CO>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[C:34]3[CH2:35][CH2:36][CH2:37][CH:38]([C:41]([OH:43])=[O:42])[CH2:39][CH2:40][C:33]=3[O:32][N:31]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 19899037HCID 19899037, compoundHCID 19899104HCID 19899104, compound

Product 1

HCID 19899117HCID 19899117, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

3 g (0.0094 mol) of a mixture of methyl 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-6-carboxylate and methyl 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-7-carboxylate were dissolved in 75 ml of methanol. 1.5 g of potassium hydroxide and 7 ml of water were added and the mixture was stirred at 20° C. for 18 hours. The methanol was removed by evaporation and an excess of water was added. The mixture was extracted twice with ethyl acetate and the aqueous phase was acidified with 2N hydrochloric acid. The aqueous-acidic layer was extracted three times with ethyl acetate and the combined ethyl acetate extracts were washed with sodium chloride solution and dried over magnesium sulfate. After evaporation and several crystallizations of the residue from ethyl acetate/hexane, there was obtained 0.78 g of 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-7-carboxylic acid of melting point 147°-150° C.

Workup

  1. customThe methanol was removed by evaporation
  2. additionan excess of water was added
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. extractionThe aqueous-acidic layer was extracted three times with ethyl acetate
  5. washthe combined ethyl acetate extracts were washed with sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation and several crystallizations of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-67f8c706092d4e47abcd3eb3fef3774e
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

Loading…