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

HRID 1468769노트

반응식

HRID 1468769 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 193813914-(4-Hydroxymethylphenyl)cyclohexanone수율 62%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-94209a6fbf184fb3a7b26c6517f76eac
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006232B2

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