Water → 1,6-Dimethyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde

HRID 1413580

反応式

HRID 1413580 の反応式
[Cl-].[Cl-].C([Al+2])C.[CH3:6][C:7]([CH3:15])=[CH:8][CH2:9][CH2:10][C:11]([CH:13]=[CH2:14])=[CH2:12].[CH3:16][C:17](=[CH:20][CH3:21])[CH:18]=[O:19].O>C1C=CC=CC=1.[Cl-].[Cl-].C([Al+2])C>[CH3:16][C:17]1([CH:18]=[O:19])[CH:20]([CH3:21])[CH2:12][C:11]([CH2:10][CH2:9][CH:8]=[C:7]([CH3:15])[CH3:6])=[CH:13][CH2:14]1

参加物

7

反応物 4

HCID 962WaterHCID 103362-Methyl-2-butenalHCID 31253MyrceneHCID 16686341Ethyl aluminium dichloride

生成物 1

HCID 198615741,6-Dimethyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde収率 44.7%

試薬・触媒・溶媒 2

HCID 16686341Ethyl aluminium dichloride触媒HCID 241Benzene溶媒4 回

反応条件

温度
60 °C

実験手順

A 3-neck reaction vessel is charged with 100 ml benzene and 50 grams of 25% ethyl aluminum dichloride in benzene. A solution containing 320 grams myrcene (85% pure), 170 grams 2-methyl-2-butenal, and 200 ml benzene is fed in at 40°-50° C. over a 1 hour period. The temperature is then raised to 60° C. and held there for 1/2 hour. An additional 10 grams ethyl aluminum dichloride solution mixed with 20 ml benzene is added and heating is continued for an additional 1/2 hour. The mixture is then cooled, water is added and the layers are separated. The organic layer is washed with water and distilled without fractionation to free the material of residue. Redistillation through an 18" Goodlow packed column provides 199 grams of 1,6-dimethyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde (b.p. 105° C., 0.9 mm).

後処理

  1. waitheld there for 1/2 hour
  2. additionis added
  3. temperatureheating
  4. waitis continued for an additional 1/2 hour
  5. temperatureThe mixture is then cooled
  6. customthe layers are separated
  7. washThe organic layer is washed with water
  8. distillationdistilled without fractionation
  9. distillationRedistillation through an 18"

出典と根拠

ORDレコード
ord-7cae96dee7504eec9c7d35766df2494a
出典データセット
uspto-grants-1981_02
特許番号
US04250338

関連ノート

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