Formaldehyde → Ethyl 2-phenylacrylate

HRID 851009Notes

Reaction equation

HRID 851009 reaction equation
C=O.[Na].O=[C:5]([CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])C(OCC)=O.C([O-])([O-])=O.[K+].[K+]>O>[C:12]([O:14][CH2:15][CH3:16])(=[O:13])[C:11]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH2:5]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 70482280Diethyl 2-oxo-3-phenylsuccinate sodium salt

Product 1

HCID 89651Ethyl 2-phenylacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

225 ml of 37 weight percent aqueous formaldehyde solution are added dropwise with stirring to a solution of 316 g of diethyl 2-oxo-3-phenylsuccinate sodium salt and 560 ml of water. During the addition, the mixture is maintained at a temperature below 25° C. The mixture is stirred for one hour at room temperature and then 152 g of anhydrous K2CO3 are added in portions over a ten minute period, while the temperature is maintained below 25° C. The resultant mixture is vigorously stirred for 1.5 hours at room temperature under a nitrogen atmosphere. The reaction mixture is diluted with 1500 ml of water and extracted with one 2.5 l. portion of ether followed by two 1.25 l portions of ether. The ether is removed and a product comprising an oil of ethyl atropate is obtained.

Workup

  1. additionDuring the addition
  2. temperaturethe mixture is maintained at a temperature below 25° C
  3. temperatureis maintained below 25° C
  4. extractionextracted with one 2.5 l
  5. customThe ether is removed
  6. customis obtained

Sources & evidence

ORD record
ord-8aaf974f22b14fd5b5561505aebcd1ba
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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