Potassium Hydroxide → HCID 53742120, compound

HRID 1731309Notes

Reaction equation

HRID 1731309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][C:18]([O:20]CC)=[O:19])=[C:5]([CH3:23])[C:4]=1[CH3:24].[OH-].[K+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][C:18]([OH:20])=[O:19])=[C:5]([CH3:23])[C:4]=1[CH3:24]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53723657HCID 53723657, compound

Product 1

HCID 53742120HCID 53742120, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 6.1 g (0.019 mol) of the ethyl ester of Example 1 was dissolved in 15 mL of ethanol and a solution of KOH (1.6 g, 0.028 mol) in 5 mL of ethanol and 1 mL of water was added. The mixture was stirred under nitrogen for 18 hrs and ethanol was evaporated in vacuo. The residue was dissolved in 100 mL of water and the resulting mixture extracted with three 20 mL-portions of ethyl acetate. The organic layers were discarded. The aqueous layer was cooled in an ice bath and acidified to pH 3 with 10N hydrochloric acid. The yellow precipitate was extracted into ethyl acetate, washed with brine and dried. Evaporation of solvent in vacuo afforded a yellow substance. Crystallization from ether gave 0.8 g of the product as yellow crystals: mp 187°-189° C.; MS-298 (m+); UV(MeOH) λmax 340 nm.

Workup

  1. customethanol was evaporated in vacuo
  2. dissolutionThe residue was dissolved in 100 mL of water
  3. extractionthe resulting mixture extracted with three 20 mL-portions of ethyl acetate
  4. temperatureThe aqueous layer was cooled in an ice bath
  5. extractionThe yellow precipitate was extracted into ethyl acetate
  6. washwashed with brine
  7. customdried
  8. customEvaporation of solvent in vacuo
  9. customafforded a yellow substance
  10. customCrystallization from ether

Sources & evidence

ORD record
ord-8a3fdee7649e4a70a2db30ecfd696050
Source dataset
uspto-grants-1986_11
Patent number
US04621099

Reaction notes

Loading…