Formaldehyde → Ethyl alpha-(phenethyl)acrylate

HRID 233371Notes

Reaction equation

HRID 233371 reaction equation
C(OC([CH:6]([CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C)C(O)=O)=O)C.C(N[CH2:21][CH3:22])C.C=[O:24].[CH2:25]([O:27][CH2:28]C)[CH3:26]>>[C:12]1([CH2:10][CH2:6][C:21](=[CH2:22])[C:28]([O:27][CH2:25][CH3:26])=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 8021DiethylamineHCID 18980811HCID 18980811, compound

Product 1

HCID 11117162Ethyl alpha-(phenethyl)acrylateYield 71%

Conditions

Temperature
20 °C

Procedure

To the 2-ethoxycarbonyl-3-phenylbutanoic acid (3.5 g) is added diethylamine (1.53 mL, 1 eq) and 30% formaldehyde (1.78 mL) at 0° C. The mixture is stirred overnight at a temperature of about 20° C. and is then taken up with diethyl ether (100 mL). The organic phase is separated after settling takes place, washed with 10% aqueous citric acid solution (40 mL) and finally dried over sodium sulphate. After filtering and concentrating to dryness, 2.2 g of ethyl 2-(phenylethyl)acrylate is obtained in a 71% yield in the form of a yellow oil, having the following characteristics: Rf =0.86 [methylene chloride/methanol (9:1 by volume)].

Workup

  1. customThe organic phase is separated
  2. washwashed with 10% aqueous citric acid solution (40 mL)
  3. dry with materialfinally dried over sodium sulphate
  4. filtrationAfter filtering
  5. concentrationconcentrating to dryness

Sources & evidence

ORD record
ord-0b3ca5abf3884ec2a045da47e4ad1a7d
Source dataset
uspto-grants-1997_01
Patent number
US05591891

Reaction notes

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