alpha-Phenylcinnamic acid, (Z)- → 1504-52-5

HRID 1609247Notes

Reaction equation

HRID 1609247 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C:15]1(/[C:21](=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)/[C:22](O)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[C:15]1(/[C:21](=[CH:25]/[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)/[CH2:22][OH:23])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 700622alpha-Phenylcinnamic acid, (Z)-HCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 60381311504-52-5

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Sodium bis-(2-methoxyethoxy)aluminum hydride (70% in toluene) (Vitride®, 536 g, 1.86 mol) was diluted with 850 mL of toluene and the solution was cooled to -10° C. under a nitrogen atmosphere. A 170 g (0.74 mol) sample of Z-2,3-diphenyl propenoic acid was added portionwise to the Vitride solution while maintaining the temperature of the reaction mixture below 10° C. The resulting mixture was stirred at 0°-5° C. until thin layer chromatography indicated total consumption of the carboxylic acid (1.5 hours). A 1.7 L sample of n-butanol was added slowly at about 25° C. until the exotherm and foaming subsided. The speed of addition of the butanol was increased as the exotherm and-foaming stabilized. The pH of the resulting cloudy mixture was adjusted from 11 to 3.5-4.0 with 1.66 L of 3N aqueous HCl. The layers were separated. The organic layer was washed two times with water and dried (Na2SO4). The mixture was filtered and the drying agent was washed with 1:1 n-butanol:toluene (500 mL). The filtrate was evaporated in vacuo to give 170 g of an amber oil which crystallized on the addition of 50 mL of toluene and 510 mL of heptane. The solid precipitate was collected, washed with heptane, and dried to a constant weight under vacuum at 40° C.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture below 10° C
  2. customconsumption of the carboxylic acid (1.5 hours)
  3. additionA 1.7 L sample of n-butanol was added slowly at about 25° C. until the exotherm and foaming
  4. additionThe speed of addition of the butanol
  5. temperaturewas increased as the exotherm and-foaming
  6. customThe layers were separated
  7. washThe organic layer was washed two times with water
  8. dry with materialdried (Na2SO4)
  9. filtrationThe mixture was filtered
  10. washthe drying agent was washed with 1:1 n-butanol
  11. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f2484c6ede1141bc82df1b448264172c
Source dataset
uspto-grants-1995_03
Patent number
US05399708

Reaction notes

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