Potassium Hydroxide → HCID 20061655, compound

HRID 1085201Notes

Reaction equation

HRID 1085201 reaction equation
C([O:3][C:4]([C:6]1[CH:28]=[CH:27][CH:26]=[CH:25][C:7]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:24])[CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:12][CH:11]=1)=[O:5])C.[OH-].[K+]>O.C(O)C>[C:4]([C:6]1[CH:28]=[CH:27][CH:26]=[CH:25][C:7]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:24])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20061646HCID 20061646, compound

Product 1

HCID 20061655HCID 20061655, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 14 g of ethyl 4-[4-(2-ethoxycarbonylbenzyloxy)-phenyl]pentanoate, 31 g of potassium hydroxide in 40 ml of water and 250 ml of 95% of ethanol was heated under reflux overnight. The solution was concentrated and the residue was dissolved in water, cooled and acidified with cold conc hydrochloric acid. The mixture was extracted with ether, and the extract was dried over anhydrous sodium sulfate, filtered and evaporated. Trituration with hexane afforded 8.9 g (72%) of product, mp 104°-106°. Recrystallization from acetonitrile gave an analytical sample, mp 115°-117.5°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in water
  5. temperaturecooled
  6. extractionThe mixture was extracted with ether
  7. dry with materialthe extract was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-367537ac36154a0f96bb339193286412
Source dataset
uspto-grants-1991_04
Patent number
US05008285

Reaction notes

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