Carbon Dioxide → HCID 59683707, compound
Reaction equation
[F:1][CH:2]([CH2:12][CH:13]([F:17])CCC)[CH2:3]COC1C=CC=CC=1.C([Li])CCC.[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C:29](=[O:31])=[O:30].Cl.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>>[CH2:37]([O:36][C:35]1[CH:34]=[C:13]([F:17])[C:12]([C:29]([OH:31])=[O:30])=[C:2]([F:1])[CH:3]=1)[CH2:33][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]Participants
Conditions
- Temperature
- -78 °C
Procedure
27.9 g of the compound (18) dissolved in 250 mL of THF were cooled at −78° C. in an argon atmosphere; thereto were then dripped 88 mL of a 1.6 M/L n-butyllithium/hexane solution, with stirring for 2 hours at the same temperature. After addition of a suitable amount of crushed dry ice, the temperature was raised to room temperature, followed by stirring overnight. 200 mL of 3N hydrochloric acid were then added under ice cooling, the organic layer was separated, and the aqueous layer was extracted with diethyl ether. The organic layers were combined, were washed with saturated brine, and were then dried over anhydrous magnesium sulfate. After evaporating the solvent, the organic layer was recrystallized from hexane to yield 17.9 g (62.4 mmol) of 4-octyloxy-2,6-difluorobenzoic acid (19).
Workup
- temperaturethe temperature was raised to room temperature
- stirringby stirring overnight
- customthe organic layer was separated
- extractionthe aqueous layer was extracted with diethyl ether
- washwere washed with saturated brine
- dry with materialwere then dried over anhydrous magnesium sulfate
- customAfter evaporating the solvent
- customthe organic layer was recrystallized from hexane
Sources & evidence
- ORD record
- ord-59d00cbf7d57462e9e2714311ce18ed2
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09059410B2
Reaction notes
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