Ethylene Glycol → 1-(4-CHLOROPHENYL)-4-OXOCYCLOHEXANECARBOXYLIc acid

HRID 1576205ノート

反応式

HRID 1576205 の反応式
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([Cl: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]([Cl: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 122302381-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrile2 回

生成物 1

HCID 204534561-(4-CHLOROPHENYL)-4-OXOCYCLOHEXANECARBOXYLIc acid収率 82.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 21.87 g. (0.079 mole) of 4-cyano-4-(4-chlorophenyl)cyclohexanone, ethylene ketal (prepared in Example 19) and 22 g. of potassium hydroxide in 220 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 and the solid remaining is recrystallized from a mixture of ethylene chloride and Skellysolve B to give 19.26 g. (82.2% yield) of 4-carboxy-4-(4-chlorophenyl)cyclohexanone, ethylene ketal, having a melting point of 162.5° to 164.5°C.

後処理

  1. additionA mixture of 21.87 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. customthe solid remaining is recrystallized from a mixture of ethylene chloride and Skellysolve B
  8. customto give 19.26 g

出典と根拠

ORDレコード
ord-9e51990ebb644347a7484e0565a0feee
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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