Acetyl chloride → HCID 22490902, compound
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2([CH3:22])[CH3:21])=[CH:13][CH:12]=1>ClCCl>[CH3:9][O:10][C:11]1[C:12]([C:5](=[O:7])[CH3:6])=[CH:13][C:14]2[CH2:15][CH2:16][CH2:17][C:18]([CH3:22])([CH3:21])[C:19]=2[CH:20]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of aluminum chloride (1-2 g, 90 mmol) in dichloromethane (300 mL) at 0° C. was added acetyl chloride (6.8 ml, 90 mmol). After stirring at 0° C. for 20 min the mixture turned into clear solution. The mixture was then cooled to −78° C. and 7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound A-85, 13.2 g, 69 mmol) in dichloromethane (20 mL) was added. After stirring at 78° C. for 2 h the mixture was poured onto ice and extracted with diethyl ether. The combined organic layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 10% ethyl acetate in hexane) to give the title compound as a white solid.
Workup
- temperatureThe mixture was then cooled to −78° C.
- stirringAfter stirring at 78° C. for 2 h the mixture
- additionwas poured onto ice
- extractionextracted with diethyl ether
- washThe combined organic layers were washed with water, brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified by flash chromatography (silica gel, 10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-2496af04685946ca89fca873595290d1
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06887896B1
Reaction notes
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