Sodium Bicarbonate → 3-[2-Hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one

HRID 1660049노트

반응식

HRID 1660049 반응식
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].[H][H]>[Pd].C(O)C>[CH3:23][C:15]([C:13]1[CH:12]=[CH:11][C:10]([CH:24]2[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]2)=[C:9]([OH:8])[CH:14]=1)([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 127881893-[2-(Benzyloxy)-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-oneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 127881913-[2-Hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one수율 62%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of 19.5 g. (0.0468 mol.) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohexanone, 12.3 g. of sodium bicarbonate, 3.00 g. of 10% palladium-on-carbon and 250 ml. of ethanol was stirred under one atmosphere of hydrogen pressure for 1.5 hours. The reaction mixture was then filtered through diatomaceous earth with ethyl acetate and the filtrate evaporated to a solid. The crude solid was purified via column chromatography on 280 g. of silica gel eluted with 20% ethercyclohexane to yield a solid. Recrystallization of this solid from aqueous methanol gave 9.1 g. (62%) of the title product, m.p. 87° C., principally in the hemiketal form.

후처리

  1. additionA mixture of 19.5 g
  2. filtrationThe reaction mixture was then filtered through diatomaceous earth with ethyl acetate
  3. customthe filtrate evaporated to a solid
  4. customThe crude solid was purified via column chromatography on 280 g
  5. washof silica gel eluted with 20% ethercyclohexane
  6. customto yield a solid
  7. customRecrystallization of this solid from aqueous methanol
  8. customgave 9.1 g

출처 및 근거

ORD 기록
ord-6993189cc2d14430a2f83b5cf706882b
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04306097

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