Benzaldehyde → Z-2-(4-fluorophenyl)-3-phenylpropenal

HRID 653629Notes

Reaction equation

HRID 653629 reaction equation
[OH-].[Na+].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=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:3]/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)/[CH:19]=[O:20])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 111263222-(4-Fluorophenyl)acetaldehyde

Product 1

HCID 15096607Z-2-(4-fluorophenyl)-3-phenylpropenal

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

4.2 g of sodium hydroxide in 30 ml of water are added to a solution of 26.5 g of benzaldehyde in 300 ml of methanol. The reaction mixture is cooled to 10° C., and 36 g of 4-fluorophenylacetaldehyde are rapidly added, during which the solution rises to 30°-40° C. The reaction solution is stirred at 40° C. for 10 hours and then cooled and the crystals which have separated out are filtered off with suction. 31.6 g (56%) of E/Z-2-(4-fluorophenyl)-3-phenylpropenal of melting point 87°-94° C. are obtained.

Workup

  1. customrises to 30°-40° C
  2. temperaturecooled
  3. customthe crystals which have separated out
  4. filtrationare filtered off with suction

Sources & evidence

ORD record
ord-771f3ddb1bbe4fbca791b3413d88484b
Source dataset
uspto-grants-1992_07
Patent number
US05128357

Reaction notes

Loading…