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

HRID 1085030

Reaktionsgleichung

Reaktionsgleichung von HRID 1085030
[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

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 1369362,2-Dimethylchroman2×HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 1820772,2-Dimethyl-6-acetylchroman

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6351afb3a6604d1fb91e4a65e5f176d7
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006550

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