2-Methyl-5-phenyladamantan-2-ol → 1-(2-Phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone

HRID 2405743노트

반응식

HRID 2405743 반응식
[CH3:1][C:2]1([OH:18])[CH:9]2[CH2:10][CH:5]3[CH2:6][C:7]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.Cl[O-].[Na+]>C1COCC1.C(O)(=O)C.O>[C:12]1([C:7]23[CH2:6][CH:5]4[CH2:4][C:3]([C:2](=[O:18])[CH3:1])([CH2:11]2)[CH:9]([CH2:10]4)[CH2:8]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 2

HCID 120380532-Methyl-5-phenyladamantan-2-olHCID 23665760Sodium Hypochlorite

생성물 1

HCID 593749561-(2-Phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of 2-methyl-5-phenyladamantan-2-ol (300 g) in THF (710 ml) and acetic acid (160 ml) was added at 0° C. to a solution (8.3%, 3330 ml) of sodium hypochloride in water. After addition of n-tetrabutylammonium iodide (25.6 g), the mixture was heated to 25° C. within 90 minutes. After full conversion and phase separation, the organic phase was washed repeatedly with water. After full concentration of the organic phase, the residue was taken up in methanol (525 ml). Potassium hydroxide (82 g) was added and the mixture was stirred at room temperature. After adding tert-butyl methyl ether, the mixture was washed repeatedly with water. The organic solution was clarified with activated carbon and concentrated fully under reduced pressure. This gave 1-(2-phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone (320 g) as an oil.

후처리

  1. customAfter full conversion and phase separation
  2. washthe organic phase was washed repeatedly with water
  3. concentrationAfter full concentration of the organic phase
  4. additionPotassium hydroxide (82 g) was added
  5. additionAfter adding tert-butyl methyl ether
  6. washthe mixture was washed repeatedly with water
  7. concentrationconcentrated fully under reduced pressure

출처 및 근거

ORD 기록
ord-28e50e8b8c3b4731b73cbbe2ac800b44
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809325B2

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