Ethanol → (E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester

HRID 1242388Notes

Reaction equation

HRID 1242388 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([CH3:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][CH2:19][O-:20].[Na+].[Na].[CH2:23]([OH:25])[CH3:24]>>[CH2:19]([O:20][C:23](=[O:25])/[CH:24]=[CH:13]/[C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][C:11]=1[CH3:17])[CH3:18]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 2723922Sodium ethoxideHCID 27598062-Methyl 4-benzyloxybenzaldehydeHCID 5360545Sodium

Product 1

HCID 21986386(E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester

Procedure

A mixture of 11.2 g (50 mmol) of 4-benzyloxy-2-methyl-benzaldehyde [PCT Int. Appl. (2002), WO 2002/092084/A1] and of 12.33 g (55 mmol) of triethyl phosphonoacetate in 25 ml of absolute ethanol was added to a cooled solution (0° C.) of sodium ethylate (freshly prepared from 1.38 g (60 mmol) of sodium and 25 ml of absolute ethanol). Subsequently, the mixture was stirred at ambient temperature for 2 hours. Then, the solvent was evaporated and the residue was partioned between tert.-butyl methyl ether and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and finally evaporated. After crystallization from a mixture of dichloromethane and n-heptane, 12.9 g of (E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester was obtained as beige crystals (87% of theory).

Workup

  1. customThen, the solvent was evaporated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfinally evaporated
  5. customAfter crystallization
  6. additionfrom a mixture of dichloromethane and n-heptane

Sources & evidence

ORD record
ord-8ef26f53e3d44f3c9d0673f5e8cc1421
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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