HCID 57190765, compound → HCID 54017022, compound

HRID 1461397Notes

Reaction equation

HRID 1461397 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[CH:10]([CH3:11])[C:9](=[O:12])[CH:8]=[CH:7][CH2:6]1.[H][H]>CCOC(C)=O>[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:6][CH2:7][CH2:8][C:9](=[O:12])[CH:10]1[CH3:11]

Participants

4

Reactant 2

HCID 57190765HCID 57190765, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54017022HCID 54017022, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 21.8 g (0.129 mole) of the crude (5S)-5-(3-hydroxypropyl)-6-methyl-2-cyclohexene-1-one in 200 ml of EtOAc was stirred with 1.0 g 10% Pd(C) under 1 atmosphere pressure of hydrogen until a total of 2600 ml of hydrogen was consumed. The reaction mixture was then filtered through a pad of celite which was washed further with EtOAc. The combined filtrates were concentrated to give 22.0 g of the crude ketone which was chromatographed on a silica gel column (4:1, hexane/EtOAc) to give 13.5 g (50% from s-carvone) of the pure (3R)-3-(3-hydroxypropyl)-2-methycyclohexanone. B.P. 110° C./0.15 mmHg. IR (CHCl3): 1702, 3475, 3625 cm-1.

Workup

  1. customwas consumed
  2. filtrationThe reaction mixture was then filtered through a pad of celite which
  3. washwas washed further with EtOAc
  4. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-27720cfb85b94b7993f5d8de4ad7fccc
Source dataset
uspto-grants-1991_12
Patent number
US05075327

Reaction notes

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