Diethyl Ether → Benzeneacetic acid, 4-ethoxy-alpha-methylene-, ethyl ester

HRID 443926Notes

Reaction equation

HRID 443926 reaction equation
C([C:3]1[C:4](CC)=[C:5]([CH:12]([C:16](C(O)=O)=O)[C:13]([O-:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH3:11])C.C(=O)([O-])[O-].[K+].[K+].[CH3:29][CH2:30]OCC>C=O>[CH2:29]([O:15][C:13](=[O:14])[C:12]([C:5]1[CH:4]=[CH:3][C:8]([O:9][CH2:10][CH3:11])=[CH:7][CH:6]=1)=[CH2:16])[CH3:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 131711858Diethyl-2-p-ethoxyphenyl-oxaloacetate

Product 1

HCID 6454764Benzeneacetic acid, 4-ethoxy-alpha-methylene-, ethyl ester

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

The keto-ester III (143.8 g) was stirred in dilute formaldehyde solution (62 ml 37% formaldehyde+water 220 ml) and to the suspension potassium carbonate solution (54.5 g, in water 280 ml) was added dropwise. At the end of the addition, ether was added to the stirred suspension to dissolve the gummy precipitate which formed and after an additional 15 minutes, gas evolution commenced. When this gas evolution ceased (after about 2 hours) the reaction mixture was extracted with additional ether and the combined ether extracts were washed with water and evaporated after drying with Na2SO4. The yield of the ethyl-2-(p-ethoxyphenyl)acrylate (II) (isolated as a yellow oil) was 97.8 g (79.8%).

Workup

  1. additionwas added dropwise
  2. additionwas added to the stirred suspension
  3. dissolutionto dissolve the gummy precipitate which
  4. customformed and after an additional 15 minutes
  5. custom(after about 2 hours)
  6. extractionwas extracted with additional ether
  7. washthe combined ether extracts were washed with water
  8. customevaporated
  9. dry with materialafter drying with Na2SO4

Sources & evidence

ORD record
ord-4a7bf4d5069e4b74bb0fcc2db5be2c90
Source dataset
uspto-grants-1981_04
Patent number
US04262014

Reaction notes

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