HCID 53703739, compound → HCID 15249177, compound

HRID 648777Notes

Reaction equation

HRID 648777 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[CH2:13][CH:14]=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 53703739HCID 53703739, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15249177HCID 15249177, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(cis-2-phenylcyclohexyl)ethanol (3 g.) in methylene chloride (6 ml.) was added rapidly to a stirred suspension of pyridinium chlorochromate (4.8 g.) in methylene chloride (6 ml.). The mixture was stirred for 2 hours and diluted with ether (75 ml.). The supernatant solution was decanted from the black tar and filtered through diatomaceous earth. The residual tar was washed thoroughly with ether. The combined ethereal filtrate and washings were evaporated. The pale yellow oil obtained, was purified by flash chromatography on silica eluting with hexane/ether (2:1 v/v) to give (cis-2-phenylcyclohexyl)acetaldehyde (1.5 g.) as a semi-solid; NMR (CDCl3): 1.1-2.35 (10H, m), 2.4-2.7 (1H,m), 2.75-3.0 (1H,m), 7.0-7.4 (5H,m) and 9.3 (1H, br s).

Workup

  1. customThe supernatant solution was decanted from the black tar
  2. filtrationfiltered through diatomaceous earth
  3. washThe residual tar was washed thoroughly with ether
  4. customThe combined ethereal filtrate and washings were evaporated
  5. customThe pale yellow oil obtained
  6. customwas purified by flash chromatography on silica eluting with hexane/ether (2:1 v/v)

Sources & evidence

ORD record
ord-1e1c6ae0e5e74b1f800974041bd37a4b
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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