Hydrogen Peroxide → HCID 178455779, compound
Reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH3:18])[CH2:13][CH2:12]1.C([Li])CCC.B(OC)(OC)[O:25]C.OO>C1COCC1.C1(C)C=CC=CC=1.O>[F:8][C:7]1[C:2]([F:1])=[C:3]([O:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)[CH:4]=[CH:5][C:6]=1[OH:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
37 g of 2,3-difluoro-1-(trans-4-ethylcyclohexyl)methoxybenzene was dissolved in 222 mL of THF, and 59.9 mL of butyllithium (2.67 M hexane solution) was added dropwise thereto at an internal temperature of −40° C. or lower. Then, further stirring was continued for 30 min. To this solution, 18.1 g of trimethyl borate was added dropwise at an internal temperature of −40° C. or lower, and then the temperature was increased to 0° C. Then, 24.7 mL of 30% hydrogen peroxide solution was added dropwise for 5 min, and the stirring was continued for 3 hours. Water and toluene were added thereto, and the organic layer was fractioned while the aqueous layer was extracted with toluene. The organic layers were combined and washed with water, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, to thereby obtain 20 g of 2,3-difluoro-4-(trans-4-ethylcyclohexyl)methoxyphenol.
Workup
- customat an internal temperature of −40° C.
- waitthe stirring was continued for 3 hours
- extractionwas extracted with toluene
- washwashed with water
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-8ff1c2e48b7e4e9b88097487ba678c1b
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003006B2
Reaction notes
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