Dimethyl Sulfoxide → 16-Methoxymethoxyhexadecanal
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31].[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[CH3:11][O:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[O:31]Participants
Procedure
To a solution of 1.23 ml of oxalyl chloride in 60 ml of dichloromethane was added dropwise at -78 ° C. a solution of 2.0 ml of dimethyl sulfoxide in 2 ml of dichloromethane. After stirring for 10 minutes, a solution of 2.13 g of 16-methoxymethoxyhexadecanol in 30 ml of dichloromethane was added dropwise and the mixture was allowed to slowly rise up to -20° C. and then stirred for 15 minutes. 5.9 ml of triethylamine was added and the mixture was stirred at 0° C. for one hour. To the reaction solution was added a saturated aqueous solution of ammonium chloride and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, distilled under reduced pressure and chromatographed over a silica gel column to afford the title compound as a colorless oily substance.
Workup
- customto slowly rise up to -20° C.
- stirringstirred for 15 minutes
- stirringthe mixture was stirred at 0° C. for one hour
- extractionextracted with chloroform
- dry with materialThe extract was dried over anhydrous sodium sulfate
- distillationdistilled under reduced pressure
- customchromatographed over a silica gel column
Sources & evidence
- ORD record
- ord-5b7c52f46ddd45f899f8ec63288b7ace
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972943
Reaction notes
Loading…