Carbon Dioxide → HCID 22152443, compound
Reaction equation
[CH2:1]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CCCCCC.C([Li])CCC.[C:29](=[O:31])=[O:30]>CCOCC>[CH2:1]([C:13]1[O:14][C:15]([C:29]([OH:31])=[O:30])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 30.4 g (0.2 moles) of 2-dodecylfuran in 300 ml of anhydrous ether is stirred at -20° C. after which 0.22 moles (92 ml of a 2.4 molar hexane solution) of butyllithium is added slowly with stirring. The reaction mixture is stirred for 1 hour then poured over 200 g of crushed dry ice (solid CO2) after which the mixture is allowed to stand for 1 hour prior to dilution with a saturated ammonium chloride solution The organic layer is separated, washed with water and brine, dried over sodium sulfate and evaporated to give 5-dodecyl-2-furancarboxylic acid. The thus obtained acid in 500 ml of anhydrous ether is stirred at room temperature during which time 200 ml of a 2 molar solution of methyllithium in ether is added slowly. The reaction mixture is allowed to stand at room temperature for 2 hours after which it is poured into a saturated ammonium chloride solution The organic layer is separated and washed with water and brine, dried over sodium sulfate and evaporated to dryness to give white crystals of methyl 2-(5-dodecylfuryl) ketone. M.P. 35°-7° C.
Workup
- additionis added slowly
- stirringThe reaction mixture is stirred for 1 hour
- customto dilution with a saturated ammonium chloride solution The organic layer is separated
- washwashed with water and brine
- dry with materialdried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-7b2f82b167804438990233c4f1e66170
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04980371
Reaction notes
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