3-Cyclohexene-1-carboxaldehyde → Z-2-(4-fluorophenyl)-3-(3-cyclohexenyl)-propenal

HRID 654464

Reaction equation

HRID 654464 reaction equation
[OH-].[Na+].[CH:3]1([CH:9]=O)[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]=[O:20])=[CH:14][CH:13]=1>O.CO>[F:11][C:12]1[CH:17]=[CH:16][C:15](/[C:18](=[CH:9]/[CH:3]2[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]2)/[CH:19]=[O:20])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 75083-Cyclohexene-1-carboxaldehydeHCID 14798Sodium HydroxideHCID 111263222-(4-fluorophenyl)acetaldehyde

Product 1

HCID 21615834Z-2-(4-fluorophenyl)-3-(3-cyclohexenyl)-propenalYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

5.5 g of sodium hydroxide in 30 ml of water are added to a solution of 40 g of 3-cyclohexenecarbaldehyde in 300 ml of methanol. The reaction mixture is cooled to 10° C., and 49.7 g of 4-fluorophenylacetaldehyde are rapidly added dropwise, the temperature of the solution not exceeding 30° C. After the mixture has been stirred for 2 hours at room temperature, 200 ml of water are added to the colorless reaction solution and the resulting emulsion is extracted by shaking with methyl tert-butyl ether. The organic phase is separated off, and 34 g (41%) of Z-2-(4-fluorophenyl)-3-(3-cyclohexenyl)-propenal are obtained under 0.5 mbar and at 136°-142° C. by distillation of the remaining residue.

Workup

  1. customexceeding 30° C
  2. extractionthe resulting emulsion is extracted
  3. stirringby shaking with methyl tert-butyl ether
  4. customThe organic phase is separated off

Sources & evidence

ORD record
ord-3d8f3edfab3d4102a408ac7aad6c81e4
Source dataset
uspto-grants-1992_07
Patent number
US05132318

Linked notes

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