Acetic Acid → Ethyl-2-p-ethoxyphenyl-3-hydroxypropionate

HRID 443928Notes

Reaction equation

HRID 443928 reaction equation
[O-:1][CH2:2]C.[Na+].[CH2:5]([O:7][C:8](=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)[CH3:6].C=O.C(O)(=O)C>C(O)C.CS(C)=O>[CH2:5]([O:7][C:8](=[O:19])[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)[CH2:2][OH:1])[CH3:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 181675Ethyl 4-ethoxyphenylacetateHCID 2723922Sodium ethoxide

Product 1

HCID 54407388Ethyl-2-p-ethoxyphenyl-3-hydroxypropionate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

Sodium ethoxide solution in ethanol (0.5 M, 18 ml) was added to a solution of ethyl-p-ethoxyphenylacetate (30 g) in dry dimethyl sulphoxide (180 ml) under argon cover. The mixture was stirred for 5 minutes and dry paraformaldehyde (5.4 g) added. After 19 h stirring, acetic acid (1.5 ml) was added, the solution quenched in ice and extracted with ether. The ether layer was washed with sodium bicarbonate solution and water, dried over anhydrous sodium sulphate, and the solvent evaporated. The resulting oil crystallized from petroleum ether (40°-60°) to yield 27.8 g product m.p. 35°-36° C.

Workup

  1. stirringAfter 19 h stirring
  2. customthe solution quenched in ice
  3. extractionextracted with ether
  4. washThe ether layer was washed with sodium bicarbonate solution and water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customthe solvent evaporated
  7. customThe resulting oil crystallized from petroleum ether (40°-60°)

Sources & evidence

ORD record
ord-5f6c4d5936754fc2b6449622365fb881
Source dataset
uspto-grants-1981_04
Patent number
US04262014

Reaction notes

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