Cetyl Alcohol → Hexadecyl Cyanoacetate

HRID 2040416노트

반응식

HRID 2040416 반응식
[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]

참가 물질

8

반응물 4

HCID 2682Cetyl Alcohol2회HCID 8058HexaneHCID 9740Cyanoacetic acidHCID 10868Dicyclohexylcarbodiimide

생성물 1

HCID 10049542Hexadecyl Cyanoacetate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1dbd6271138d44ce99e84b725563ac0c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580820B2

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