O-Xylene → Sodium 2-cyclopropyl-6-methylphenoxide
Reaction equation
[OH-].[Na+:2].C1(C)C(C)=CC=CC=1.[CH:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=2[OH:21])[CH2:13][CH2:12]1>O>[CH:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=2[O-:21])[CH2:13][CH2:12]1.[Na+:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
115.4 g of pure water was added to 54.1 g (1.312 mol) of 97% sodium hydroxide and heated to 50° C. to dissolve sodium hydroxide, and then xylene (1,000 ml) was added to the resultant solution at room temperature. To the mixture was added dropwise 200 g (1.317 mol) of 2-cyclopropyl-6-methylphenol at room temperature over 20 minutes. The resultant two-phase solution was subjected to thermal dehydration at 140° C., and, after completion of the distilling off of water, the resultant solution was cooled to 5° C. to obtain a slurry. The obtained slurry was subjected to filtration under a reduced pressure, and the resultant solids were washed with 500 ml of hexane twice. The solids were dried under a reduced pressure, and the resultant solids were quantitatively determined by an HPLC internal standard analysis method, which showed that 150.2 g of sodium 2-cyclopropyl-6-methylphenoxide (yield: 67%) was obtained.
Workup
- customwas subjected to thermal dehydration at 140° C.
- customto obtain a slurry
- filtrationThe obtained slurry was subjected to filtration under a reduced pressure
- washthe resultant solids were washed with 500 ml of hexane twice
- customThe solids were dried under a reduced pressure
Sources & evidence
- ORD record
- ord-c3429dd143d549948648a95cca71dbfa
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552182B2
Reaction notes
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