Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-(4-Hydroxymethylphenyl)cyclohexanone

HRID 1468769Notes

Reaction equation

HRID 1468769 reaction equation
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:25][CH2:24][C:19]3(OCC[O:20]3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)(C)C)(C)(C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[OH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68160088HCID 68160088, compound

Product 1

HCID 193813914-(4-Hydroxymethylphenyl)cyclohexanoneYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl-[4-(1,4-dioxa-spiro[4.5]dec-8-yl)benzyloxy]dimethylsilane (12.1 g, 33.3 mmol) in acetone (12 ml) and water (1.2 ml) was added pyridinium p-toluenesulfonate (2.51 g, 9.99 mmol) at room temperature. The mixture was refluxed for 3 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40) to afford 4-(4-hydroxymethylphenyl)cyclohexanone as a colorless solid (4.21 g, 20.6 mmol, 62%).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40)

Sources & evidence

ORD record
ord-94209a6fbf184fb3a7b26c6517f76eac
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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