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

HRID 1660049ノート

反応式

HRID 1660049 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6993189cc2d14430a2f83b5cf706882b
出典データセット
uspto-grants-1981_12
特許番号
US04306097

反応ノート

読み込み中…