Hydrochloric Acid → 4-Dimethylamino-4-phenylcyclohexanecarbaldehyde
Reaction equation
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[CH3:26][N:27]([CH3:41])[C:28]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.Cl>CN(C=O)C>[CH3:26][N:27]([CH3:41])[C:28]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:33][CH2:32][CH:31]([CH:2]=[O:3])[CH2:30][CH2:29]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under argon, methoxymethyltriphenylphosphonium chloride (6.3 g, 18.4 mmol) was dissolved in DMF (25 ml), and sodium hydride (60 wt. % in mineral oil, 737 mg, 18.4 mmol) was added. A solution of 4-dimethylamino-4-phenylcyclohexanone (2.0 g, 9.2 mmol) in 25 ml of DMF was added dropwise over 30 min and the suspension was stirred for 3 d at RT. For the work-up, the suspension was poured slowly into 2 M HCl (50 ml) cooled with ice-water, stirred at RT for 2 h and then extracted with diethyl ether (5×25 ml) and EE (6×20 ml). The aqueous phase was then brought to pH 10-11 with 1 M NaOH and extracted with EE (5×20 ml). The combined extracts were dried with sodium sulfate, filtered and concentrated. The residue was 4-dimethylamino-4-phenylcyclohexanecarbaldehyde (2.0 g of brown oil) in a diastereoisomer ratio of 55:45 (1H NMR).
Workup
- stirringstirred at RT for 2 h
- extractionextracted with diethyl ether (5×25 ml) and EE (6×20 ml)
- extractionextracted with EE (5×20 ml)
- dry with materialThe combined extracts were dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-204b8cdce7854b53be02ed2cfc8b1c1e
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07232847B2
Reaction notes
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