Dichloromethane → Benzeneethanol, 4-octyl-, 1-methanesulfonate
Reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].ClCCl.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>O>[CH3:28][S:29]([O:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=1)(=[O:31])=[O:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(4-Octylphenyl)ethanol (53 g) and dichloromethane (500 mL) are charged into a 1 liter three-neck round bottom flask equipped with guard tube and addition funnel. Triethylamine (83.5 g) is added, the mixture is stirred for 30 minutes, then it is cooled to 0° C. Methanesulphonyl chloride (35.2 mL) is added drop-wise at 0° C. and the mass is stirred for 3 hours at room temperature. The mass is diluted with water (700 mL) and the organic layer is separated and the aqueous layer is extracted with dichloromethane (2×250 mL). The combined organic layers is washed with saturated sodium bicarbonate (500 mL) and brine solution (500 mL). The organic layer is separated, dried with sodium sulphate, and concentrated under vacuum to obtain the title compound. Yield: 70 g.
Workup
- customequipped with guard tube and addition funnel
- stirringthe mass is stirred for 3 hours at room temperature
- customthe organic layer is separated
- extractionthe aqueous layer is extracted with dichloromethane (2×250 mL)
- washThe combined organic layers is washed with saturated sodium bicarbonate (500 mL) and brine solution (500 mL)
- customThe organic layer is separated
- dry with materialdried with sodium sulphate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-1a1b93bd92454003970afd1ad09040cf
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216943B2
Reaction notes
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