Potassium Hydroxide → HCID 68145100, compound

HRID 918270Notes

Reaction equation

HRID 918270 reaction equation
C([O:4][C@H:5]1[CH2:9][CH2:8][C@@H:7]([CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH2:11]2)[C@:6]1([CH3:26])[CH2:22][C:23]([OH:25])=[O:24])(=O)C.[OH-].[K+]>CO.O>[CH3:21][O:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([C@H:7]1[C@:6]([CH3:26])([CH2:22][C:23]([OH:25])=[O:24])[C@@H:5]([OH:4])[CH2:9][CH2:8]1)[CH2:19][CH2:18]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22791762HCID 22791762, compound

Product 1

HCID 68145100HCID 68145100, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3.33 g of (1S,2S,5S)-2-acetoxy-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-1-methylcyclo-pentaneacetic acid in 50 ml of methanol is added a solution of 3.00 g of potassium hydroxide in 15 ml of water. The resultant solution is refluxed for 2 hours, then diluted with 250 ml of water. Clarification is effected by filtration. The filtrate is acidified with hydrochloric acid. A solid precipitates which, isolated by filtration and recrystallized from a mixture of ethyl acetate and hexane, affords (1S,2S,5S)-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-2-hydroxy-1-methylcyclopentaneacetic acid melting at approximately 141.5°-142.5°. The product has a specific rotation of +65°.

Workup

  1. filtrationClarification is effected by filtration
  2. customA solid precipitates which
  3. customisolated by filtration
  4. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e270d438f8aa4d4fa16b4f9093e1d13a
Source dataset
uspto-grants-1976_07
Patent number
US03970686

Reaction notes

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