Cetyl Alcohol → Hexadecyl Cyanoacetate

HRID 2040416ノート

反応式

HRID 2040416 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 10049542Hexadecyl Cyanoacetate

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1dbd6271138d44ce99e84b725563ac0c
出典データセット
uspto-grants-2013_11
特許番号
US08580820B2

反応ノート

読み込み中…