Acetic Acid → 3-Phenyl-3-buten-2-one

HRID 12494

Reaction equation

HRID 12494 reaction equation
[C:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.N1CCCC[CH2:14]1.CC(O)=O>CO>[C:1]1([C:7](=[CH2:14])[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 7678PhenylacetoneHCID 8082Piperidine

Product 1

HCID 3247973-Phenyl-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-Phenyl-propan-2-one (40.8 g) was dissolved in 200 ml of MeOH. Formaline (37%) (79 mL), piperidine (4 ml) and HOAc (4 ml) where added and de reaction was stirred for 3 h at 60° C. The reaction mixture was evaporated to dryness under reduced pressure. The residue was taken up in diethyl ether, and extracted with water. The organic layer was washed with 1M HCl, dried over MgSO4 and evaporated under reduced pressure to yield 36.3 g of a yellow liquid. 1H NMR (400 MHz, CDCl3) δ 2.41 (s, 3H), 5.87 (s, 1H), 6.18 (s, 1H), 7.24-7.40 (m, 5H).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. extractionextracted with water
  3. washThe organic layer was washed with 1M HCl
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7f87a3c0d5dd43838f708ff5bd85a19e
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

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