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

HRID 1165387

반응식

HRID 1165387 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 16686341Ethyl aluminium dichloride촉매HCID 241Benzene용매4회

반응 조건

온도
60 °C

실험 절차

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" Goodloe 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).

후처리

  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"

출처 및 근거

ORD 기록
ord-dca29e556f0e4bae9134be75200f444a
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04909854

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