Acetyl chloride → 3-Acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone

HRID 1834538노트

반응식

HRID 1834538 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([OH:25])=[C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:7]2=[O:12].[O:27]1CC[CH2:29][CH2:28]1.[H-].[Na+].C(Cl)(=O)C>C(Cl)Cl>[C:28]([O:25][C:5]1[C:4](=[O:26])[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])[C:7](=[O:12])[C:6]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:27])[CH3:29]

참가 물질

6

반응물 4

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran4회HCID 24758Sodium hydrideHCID 178442826HCID 178442826, 화합물

생성물 1

HCID 213252433-Acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 0.95 parts of 5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone in 20 parts of anhydrous tetrahydrofuran was added under nitrogen to a mixture of 0.0635 parts of dispersed sodium hydride in 40 parts of tetrahydrofuran with stirring at room temperature. After 45 minutes of stirring, a solution of 0.275 parts of acetyl chloride in 30 parts of tetrahydrofuran was added and the mixture stirred for 5 hours. The tetrahydrofuran was stripped under reduced pressure and the residue taken up in methylene chloride and then washed with water, 10% hydrochloric acid, four more times with water, dried over sodium sulfate and stripped. The resulting yellow solid was purified by column chromatography on silica gel using 1-chlorobutane as eluent. Solvent removal gave 0.9 parts of 3-acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone, m.p. 57°-59° C.

후처리

  1. stirringAfter 45 minutes of stirring
  2. stirringthe mixture stirred for 5 hours
  3. washwashed with water, 10% hydrochloric acid, four more times with water
  4. dry with materialdried over sodium sulfate
  5. customThe resulting yellow solid was purified by column chromatography on silica gel
  6. customSolvent removal

출처 및 근거

ORD 기록
ord-67b0bf36426741e48e159885ba850f98
출처 데이터셋
uspto-grants-1978_01
특허 번호
US04070481

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