Ethylene Glycol → 1-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

HRID 1576206ノート

反応式

HRID 1576206 の反応式
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#N.[OH-:17].[K+].C(O)C[OH:21]>O>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([OH:21])=[O:17]

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

生成物 1

HCID 219553321-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid収率 93%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 18.17 g. (0.07 mole) of 4-cyano-4-(4-fluorophenyl)cyclohexanone, ethylene ketal (prepared in Example 20 and 15 g. of potassium hydroxide in 150 ml. of ethylene glycol is heated at reflux for about 16 hours. The resulting solution is allowed to cool, diluted with water and washed with ether. The aqueous layer is covered with ether and then cautiously acidified. The aqueous layer is extracted with two additional portions of ether and the extracts combined. The extracts are evaporated to dryness to give 18.2 g. (93% yield) of 4-carboxy-4-(4-fluorophenyl)cyclohexanone, ethylene ketal, having a melting point of 117° to 122°C.

後処理

  1. additionA mixture of 18.17 g
  2. temperatureat reflux for about 16 hours
  3. temperatureto cool
  4. washwashed with ether
  5. extractionThe aqueous layer is extracted with two additional portions of ether
  6. customThe extracts are evaporated to dryness
  7. customto give 18.2 g

出典と根拠

ORDレコード
ord-fc7c456a4a014edbb3844c4bdd824d1b
出典データセット
uspto-grants-1976_09
特許番号
US03979444

反応ノート

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