Potassium Hydroxide → 2-[(4-Fluorophenyl)methyl]heptanedioic acid

HRID 326008ノート

反応式

HRID 326008 の反応式
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]=1

参加物

7

反応物 4

HCID 14797Potassium HydroxideHCID 680214-Fluorobenzyl bromideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 2723922Sodium ethoxide

生成物 1

HCID 135197692-[(4-Fluorophenyl)methyl]heptanedioic acid収率 87.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

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.

後処理

  1. customto form a mixture which
  2. extractionsubjected to extraction with ethyl ether
  3. customto obtain a residue
  4. temperaturerefluxed for 3 hours

出典と根拠

ORDレコード
ord-8c2c92b7eb6048f18bafb815685ead19
出典データセット
uspto-grants-1984_04
特許番号
US04443626

反応ノート

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