Acetic Anhydride → 1-Phenyl-2-acetoxy-cyclohex-3-ene-1-carboxylic acid-ethyl-ester

HRID 1076765

Reaction equation

HRID 1076765 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[CH:14](=O)/[CH:15]=[CH:16]/[CH3:17].[C:19]([O-:22])(=[O:21])[CH3:20].[Na+].CC(OC(C)=O)=O>>[CH2:12]([O:11][C:1]([C:2]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:17][CH2:16][CH:15]=[CH:14][CH:3]1[O:22][C:19](=[O:21])[CH3:20])=[O:10])[CH3:13]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 89651Ethyl 2-phenylacrylateHCID 447466CrotonaldehydeHCID 517045Sodium Acetate

Product 1

HCID 213945641-Phenyl-2-acetoxy-cyclohex-3-ene-1-carboxylic acid-ethyl-ester

Procedure

1 mole (170 g) of ethyl atropate, 210 g of crotonaldehyde, 150 g of anhydrous sodium acetate and 0.6 l of acetanhydride are heated to boiling for 6 h. while stirring. Subsequently the main amount of the liquid phase is distilled off under vacuum, and the residue is extracted with 1 liter of hot ligroin. The residue of the ligroin phase is distilled. The product -- although being pure according to gas chromatography -- distills in a wide boiling range: b.p.0,1 130°-165°C. Yield: 105 g. It crystallizes when allowed to stand. M.P. 72°-73°C (from petroleum ether).

Workup

  1. distillationSubsequently the main amount of the liquid phase is distilled off under vacuum
  2. extractionthe residue is extracted with 1 liter of hot ligroin
  3. distillationThe residue of the ligroin phase is distilled
  4. distillationdistills in a wide boiling range
  5. customb.p.0,1 130°-165°C
  6. customIt crystallizes when

Sources & evidence

ORD record
ord-5808096a9b3a408da98d04f50da4b71d
Source dataset
uspto-grants-1976_05
Patent number
US03957851

Linked notes

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