Potassium Hydroxide → HCID 23442837, compound

HRID 653833Notes

Reaction equation

HRID 653833 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:28])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[K+]>C(O)C.O.CS(C)=O>[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14](=[O:28])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19890287HCID 19890287, compound

Product 1

HCID 23442837HCID 23442837, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 86745966HCID 86745966, compoundSolvent

Procedure

6 g (15 mmol) of 1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-(4-ethoxycarbonylphenoxy)ethanone (from Example 5) were stirred with 5 g of potassium hydroxide in 90 ml of ethanol/water/dimethyl sulfoxide (5:3:1) at 80° C. for 5 min and poured into ice-water, the alkaline solution was extracted with ether and the extract was discarded, and then the pH was adjusted to 3 with concentrated hydrochloric acid, and the acid solution was extracted with ethyl acetate. The latter extract was washed with water, dried over magnesium sulfate and evaporated. Recrystallization of the residue from ethanol provided 2.8 g of the title compound of melting point 168°-170° C.

Workup

  1. extractionthe alkaline solution was extracted with ether
  2. extractionthe acid solution was extracted with ethyl acetate
  3. extractionThe latter extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-859cc51c956647f0aac734114113a229
Source dataset
uspto-grants-1992_07
Patent number
US05128479

Reaction notes

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