Cetyl Alcohol → Hexadecyl Cyanoacetate
Reaction equation
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.[C:33]([CH2:35][C:36](O)=[O:37])#[N:34].CCCCCC>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[C:33]([CH2:35][C:36]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:37])#[N:34]Participants
Procedure
The esterification reaction of hexadecanol was carried under an inert atmosphere (Argon). 9.9864 g of dicyclohexylcarbodiimide (DCC) and 50 mg of 4-(dimethylamino) pyridine (DMAP), previously dissolved in 50 ml of anhydrous dichloromethane, were added to a solution of cyanoacetic acid (7.4853 g) and of hexadecanol (10.6674 g) in 50 ml of anhydrous dichloromethane plus 5 ml of ethyl acetate. The obtained sample was stirred for 24 hours at room temperature. Then 50 ml of anhydrous hexane were added. The formed solid residue was separated off by filtration under vacuum, and washed with n-hexane (70 ml). The filtrate was concentrated under reduced pressure until obtaining an amorphous yellow solid. It was afterwards purfied by flash chromatography (oil ligroin/ethyl acetate 9/1). 14 g of a white solid were thus obtained.
Workup
- customThe formed solid residue was separated off by filtration under vacuum
- washwashed with n-hexane (70 ml)
- concentrationThe filtrate was concentrated under reduced pressure
- customuntil obtaining an amorphous yellow solid
Sources & evidence
- ORD record
- ord-9adb436ca1c149018d2f40b477cf4519
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399457B2
Reaction notes
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