Phenylacetone → HCID 6512704, compound

HRID 866584Notes

Reaction equation

HRID 866584 reaction equation
[C:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11](OCC)=[O:12].[O-]CC.[Na+]>C1COCC1.O>[OH:12]/[CH:11]=[C:7](/[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)\[C:8]([CH3:9])=[O:10]

Participants

6

Reactant 3

HCID 7678PhenylacetoneHCID 8025Ethyl formateHCID 2723922Sodium ethoxide

Product 1

HCID 6512704HCID 6512704, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phenylacetone (Aldrich Chem. Co. 13,538-0; Beilstein 7, 303), XXVIa (101 g. 0.75 mol) was combined with 100 g (1.35 mol) of ethyl formate and added all at once to a suspension of 50 g (0.75 mol) of sodium ethoxide in 500 ml of THF. After 3 hours at room temperature the brown solution was diluted with 400 ml of H2O. Folloing extraction with benzene to remove unreacted starting material, the aqueous phase was acidified with dilute HCl. The product was extracted with benzene, washed with H2O, dried over MgSO4, and concentrated to give an oil. Distillation gave 39 g (0.24 mol) of (Z)-1-hydroxymethylene-1-phenylacetone, XXVIIa, as a colorless oil, bp 65°-69° C (0.3 mm).

Workup

  1. additionadded all at
  2. extractionextraction with benzene
  3. customto remove unreacted
  4. extractionThe product was extracted with benzene
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give an oil
  9. distillationDistillation

Sources & evidence

ORD record
ord-4af455d5002d4596b85adb485afd32fc
Source dataset
uspto-grants-1978_07
Patent number
US04100185

Reaction notes

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