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

HRID 1660049Notes

Reaction equation

HRID 1660049 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6993189cc2d14430a2f83b5cf706882b
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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