Water → 4-Dimethylamino-4-phenylcyclohexanecarbaldehyde

HRID 1295205Notes

Reaction equation

HRID 1295205 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[Cl-].[CH3:18][O:19]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([CH:18]=[O:19])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 104439064-Dimethylamino-4-phenylcyclohexanecarbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

46 mmol (10.0 g) of 4-dimethylamino-4-phenylcyclohexanone were dissolved in toluene. This solution was added dropwise at 70° C. to a suspension of 138.1 mmol, (47.33 g) methoxymethyl triphenylphosphonium chloride and 138.1 mmol (25.82 g) potassium tert.-butylate. The mixture was stirred for a few more hours at 70° C., hydrolysed with water and extracted using EE. The combined organic phases were washed with saturated NaCl solution, dried over sodium sulphate and concentrated. The resultant brown resin was chromatographed using silica gel. The desired aldehyde is obtained as a cis/trans-mixture.

Workup

  1. extractionextracted
  2. washThe combined organic phases were washed with saturated NaCl solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe resultant brown resin was chromatographed

Sources & evidence

ORD record
ord-4e2a7dc3bee745b7b841dc6042754eb7
Source dataset
uspto-grants-2007_07
Patent number
US07241802B2

Reaction notes

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