Acetyl chloride → 2,2-Dimethyl-6-acetylchroman

HRID 1417706노트

반응식

HRID 1417706 반응식
[CH3:1][C:2]1([CH3:12])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[C:13](Cl)(=[O:15])[CH3:14].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[C:13]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:12])([CH3:1])[CH2:11][CH2:10]2)(=[O:15])[CH3:14]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 1369362,2-Dimethylchroman2회HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 1820772,2-Dimethyl-6-acetylchroman수율 54.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,2-dimethylchroman (Compound 214, 15 g, 19.4 mmol) in dry CH2Cl2 (100 mL) was added acetyl chloride (1.52 ml, 21.3 mmol) followed by AlCl3 (2.84 g, 21.3 mmol). The reaction mixture was stirred at room temperature for 30 minutes and then poured into ice water. Extraction (CH2Cl2), drying (Na2SO4), and concentration under reduced pressure afforded a yellow oil. Column chromatography (EtOAc:hexanes 1:9) yielded 2.15 g (54%) of the title compound as a yellow solid. 1H NMR δ 7.73 (2H, m), 6.80 (1H, d, J=8.3 Hz), 2.83 (2H, t, J=6.9 Hz), 2.54 (3H, s), 1.84 (2H, t, J=6.9 Hz), 1.36 (6H, s). Anal. (C13H16O2) C, H.

후처리

  1. extractionExtraction (CH2Cl2)
  2. customdrying
  3. concentration(Na2SO4), and concentration under reduced pressure
  4. customafforded a yellow oil

출처 및 근거

ORD 기록
ord-ebea36303e0a48f1a0fb676e3452c031
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877207

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