Water → 4-Benzyl-4-methoxycyclohexanone

HRID 900081Notes

Reaction equation

HRID 900081 reaction equation
[CH2:1]([C:8]1([O:18][CH3:19])[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([C:8]1([O:18][CH3:19])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 221798428-Benzyl-8-methoxy-1,4-dioxaspiro[4.5]decane

Product 1

HCID 221798314-Benzyl-4-methoxycyclohexanoneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 11B (8.5 g, 32.5 mmol) in acetone (200 mL) was treated with water (100 mL) and p-toluenesulfonic acid monohydrate (1 g), heated to reflux, stirred overnight, and concentrated to remove the acetone. The remaining aqueous solution was extracted with ethyl acetate (3×100 mL) and the combined extracts were washed sequentially with 1N NaOH, water, and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (6.95 g, 95%). MS (CI) m/e 236.2 (M+18)+.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto remove the acetone
  5. extractionThe remaining aqueous solution was extracted with ethyl acetate (3×100 mL)
  6. washthe combined extracts were washed sequentially with 1N NaOH, water, and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d61c4df5b24041ffa6a958fd8ae46913
Source dataset
uspto-grants-2008_04
Patent number
US07358251B2

Reaction notes

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