Hydrochloric Acid → [2-(3-Methoxybenzyl)cyclohexyl]methyl acetate
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH2:13][OH:14].[C:18](OC(=O)C)(=[O:20])[CH3:19].Cl>N1C=CC=CC=1>[C:18]([O:14][CH2:13][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[CH2:6][C:5]1[CH:15]=[CH:16][CH:17]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:20])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of [2-(3-methoxybenzyl)cyclohexyl]methanol (1.5 g) in pyridine (7.5 mL) was added acetic anhydride (4.1 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at ambient temperature for 1 hour. The reaction mixture was added 1M HCl aqueous solution and was extracted with EtOAc. The organic layer was washed with 1M HCl aqueous solution and saturated NaHCO3 aqueous solution, and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford [2-(3-methoxybenzyl)cyclohexyl]methyl acetate (1.57 g) as a colorless oil.
Workup
- extractionwas extracted with EtOAc
- washThe organic layer was washed with 1M HCl aqueous solution and saturated NaHCO3 aqueous solution, and brine
- dry with materialThe organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-608214701e9c4c059c81125ff1a97335
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273745B2
Reaction notes
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