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

HRID 1085030

반응식

HRID 1085030 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].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O.O>[CH3:1][C:2]1([CH3:12])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13](=[O:15])[CH3:14])[CH:8]=2)[O:3]1

참가 물질

6

반응물 3

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

생성물 1

HCID 1820772,2-Dimethyl-6-acetylchroman

시약·촉매·용매 2

HCID 962Water용매HCID 6375Nitromethane용매

실험 절차

A solution of 5.0 g (30.82 mmol) of 2,2-dimethylchroman (Compound 56) in 50 ml of nitromethane was treated, under nitrogen, with 2.53 g (32.35 mmol) of acetyl chloride followed by 4.4 g (33 mmol) of aluminum chloride. The reaction mixture was stirred at room temperature for 3 hours and then cooled in an ice-bath and treated slowly with 50 ml of 6M HC1. The mixture was diluted with water and extracted with ether. The ether extracts were washed successively with saturated NaHCO3 solution, water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in-vacuo and the resultant residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane) to give the title compound as a white solid. PMR (CDCl3) : & 1.36 (6H, s), 1.84 (2H, t, J~6.8 Hz), 2.54 (3H, s), 2.82 (2H, t, J~6.8 Hz), 6.80 (1H, d, J~8.4 Hz), 7.69-7.76 (2H, m). MS exact mass, m/e 204.1140 (calcd. for C13H16O2, 204.1150).

후처리

  1. temperaturecooled in an ice-bath
  2. additiontreated slowly with 50 ml of 6M HC1
  3. extractionextracted with ether
  4. washThe ether extracts were washed successively with saturated NaHCO3 solution, water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in-vacuo
  7. customthe resultant residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-6351afb3a6604d1fb91e4a65e5f176d7
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05006550

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