Cetyl Alcohol → Hexadecyl Cyanoacetate

HRID 2040416Notes

Reaction equation

HRID 2040416 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].[C:18]([CH2:20][C:21](O)=[O:22])#[N:19].C1(N=C=NC2CCCCC2)CCCCC1.CCCCCC>ClCCl.C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[C:18]([CH2:20][C:21]([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:22])#[N:19]

Participants

8

Reactant 4

HCID 2682Cetyl Alcohol2×HCID 8058HexaneHCID 9740Cyanoacetic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 10049542Hexadecyl Cyanoacetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The esterification reaction of hexadecanol was carried out under an inert atmosphere (Argon). To a solution of cyanoacetic acid (7.4853 g) and of hexadecanol (10.6674 g) in 50 ml of anhydrous dichloromethane and 5 ml of ethyl acetate, 50 ml of anhydrous dichloromethane containing 9.9864 g of dicyclohexylcarbodiimide (DCC) and 50 mg of 4-(dimethylamino)pyridine (DMAP) were added. The reaction mixture was stirred for 24 hours at room temperature. Then 50 ml of anhydrous hexane were added. The formed solid residue was separated by filtration under vacuum and washed with n-hexane (70 ml). The filtrate was concentrated under reduced pressure until obtaining an amorphous yellow solid, subsequently purified by flash chromatography (ligroin/ethyl acetate 9/1 v/v), yielding 14 g of a white solid.

Workup

  1. customThe formed solid residue was separated by filtration under vacuum
  2. washwashed with n-hexane (70 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customuntil obtaining an amorphous yellow solid
  5. customsubsequently purified by flash chromatography (ligroin/ethyl acetate 9/1 v/v)

Sources & evidence

ORD record
ord-1dbd6271138d44ce99e84b725563ac0c
Source dataset
uspto-grants-2013_11
Patent number
US08580820B2

Reaction notes

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