Potassium Hydroxide → 2-[(4-Fluorophenyl)methyl]heptanedioic acid
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])=[O:5])C.[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.[O-:22]CC.[Na+].[OH-].[K+]>C(O)C.O>[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][CH:6]([C:4]([OH:3])=[O:5])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([OH:12])=[O:22])=[CH:16][CH:15]=1Participants
Procedure
19.2 g of 2-oxocyclohexanecarboxylic acid ethyl ester, 21.4 g of p-fluorobenzyl bromide, 7.7 g of sodium ethoxide and 200 ml of ethanol were mixed together to form a mixture which was refluxed for 2 hours, incorporated with 500 ml of water and subjected to extraction with ethyl ether. The resulting ether layer was freed of the ether to obtain a residue. The thus obtained residue was dissolved in 500 ml of 70% ethanol, incorporated with 16.1 g of potassium hydroxide, refluxed for 3 hours and hydrolyzed to obtain 26.5 g of 1-(4-fluorobenzyl)-1,5-pentane dicarboxylic acid having a melting point of 80°-81° C. in the colorless needle form. 26 g of the thus obtained compound in the needle form and 300 g of polyphosphoric acid were mixed together to form a mixture which was agitated at 100° C. for 3 hours. After the end of the reaction, the resulting reaction mixture was incorporated with iced water and subjected to extraction with ethyl acetate. The organic layer was washed with water, dehydrated and freed of the solvent by distilling it off, thereby to obtain a residue. The thus obtained residue was recrystallized from isopropyl ether to obtain 18.2 g of 6-fluoro-1-oxo-2,3-dihydro-2-indene valeric acid in the colorless platy form.
Workup
- customto form a mixture which
- extractionsubjected to extraction with ethyl ether
- customto obtain a residue
- temperaturerefluxed for 3 hours
Sources & evidence
- ORD record
- ord-8c2c92b7eb6048f18bafb815685ead19
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04443626
Reaction notes
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