Water → HCID 11008421, compound

HRID 1722497Notes

Reaction equation

HRID 1722497 reaction equation
Cl[CH:2]1[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.CC(C)([O-])C.[K+].O>CS(C)=O>[CH:4]1([CH2:6][O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH:2]=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14720911HCID 14720911, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11008421HCID 11008421, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

[[(3-Chlorocyclobutyl)methoxy]methyl]benzene (82 g, 0.39 mole) in 390 ml of dry dimethylsulfoxide was slowly added to a solution of potassium t-butoxide (132 g, 1.17 mole) in 390 ml of dry dimethylsulfoxide in a water-bath at 18° C. under a dry argon atmosphere. After stirring for 1 hour at room temperature, the reaction mixture was poured into 1600 ml of water and extracted with ether (3×1000 ml). The ether extracts were back-extracted with water (4×2000 ml) and the ether extract was then dried over sodium sulfate. The ether was removed in vacuo and the crude product was purified on a Merck silica column, eluting the column with 5% ethyl acetate-hexane. Appropriate fractions were combined and the solvents removed in vacuo yielding 60.0 g of the title compound as a colorless liquid.

Workup

  1. extractionextracted with ether (3×1000 ml)
  2. extractionThe ether extracts were back-extracted with water (4×2000 ml)
  3. extractionthe ether extract
  4. dry with materialwas then dried over sodium sulfate
  5. customThe ether was removed in vacuo
  6. customthe crude product was purified on a Merck silica column
  7. washeluting the column with 5% ethyl acetate-hexane
  8. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-c4e5c0a4bcd7427eba1abbf9b5f7ea06
Source dataset
uspto-grants-1989_08
Patent number
US04855466

Reaction notes

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