Hydrochloric Acid → 1-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

HRID 344943

반응식

HRID 344943 반응식
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C)([O-])=O.CCOCC>[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=2)[O:5][CH2:4][CH2:3]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 3167634,4-Dimethylchroman2회HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 134781601-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6375Nitromethane용매

실험 절차

To a stirred solution of 7.94 g (48.9425 mmol) of 4,4-dimethylchroman (Compound 76) in 70 ml of nitromethane was added under argon 4.0 g (50.96 mmol) of acetyl chloride followed by 6.8 g (51 mmol) of aluminum chloride. This was stirred at room temperature for 5.5 hours and then cooled in an ice bath and treated slowly with 70 ml of 6N hydrogen chloride. The resultant mixture was stirred at room temperature for 10 minutes and then treated with 100 ml ether and the organic layer separated. The organic layer was washed with water, saturated NaHCO3 and saturated NaCL solutions and dried (MgSO4). Solvent was removed in vacuo and the residue by flash chromatography (silica; 10% ethyl acetate in hexanes). This was followed by kugelrohr distillation (95-100 degrees C.; 0.15 mm) to give the title compound as a colorless oil. PMR (CDCl3): & 1.40 (6H), 1.95-2.00 (2H, m), 2.58 (3H), 4.25-4.30 (2H, m), 6.83 (1H, d, J~8.0 Hz), 7.62 (1H, dd, J~8.0 Hz, 1.5 Hz), 8.00 (1H, d, J~1.5 Hz).

후처리

  1. temperaturecooled in an ice bath
  2. customthe organic layer separated
  3. washThe organic layer was washed with water, saturated NaHCO3 and saturated NaCL solutions
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. distillationThis was followed by kugelrohr distillation (95-100 degrees C.; 0.15 mm)

출처 및 근거

ORD 기록
ord-a7aa161c877b46dbafc88280d573b052
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053523

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