HCID 20145924, compound → HCID 66651942, compound

HRID 418911Notes

Reaction equation

HRID 418911 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][CH:16]=[O:17].CC(C)=[O:20].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][C:16]([OH:20])=[O:17]

Participants

4

Reactant 2

HCID 20145924HCID 20145924, compoundHCID 131709961Jones' reagent

Product 1

HCID 66651942HCID 66651942, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine [2-(2-methoxy-phenyl)-cyclohexyl]-acetaldehyde (0.336 g, 1.45 mmol), and acetone (10.0 mL). Add dropwise Jones reagent until color goes from green to orange and persists for several minutes (approximately 1.0 mL). Then concentrate on rotovap then add ethyl acetate and wash excess chromium away with brine washes. Dry over anhydrous sodium sulfate, concentrate to yield the titled compound (0.301 g, 84%). TLC Rf=0.13 in 20% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.2 (m, 1H), 7.0 (m, 1H), 6.8 (m, 2H), 3.8 (s, 3H), 3.3 (m, 1H), 2.6 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H), 1.6 (m, 8H).

Workup

  1. customfor several minutes
  2. concentrationThen concentrate on rotovap then add ethyl acetate
  3. washwash excess chromium away with brine washes
  4. dry with materialDry over anhydrous sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b40c4c21cec84dbcaf2c88d3869f4a1b
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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