p-Toluenesulfonic acid → HCID 57724954, compound

HRID 1987805Notes

Reaction equation

HRID 1987805 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5](=[O:7])[CH3:6].[CH2:8](O)[C:9](C)([CH3:11])[CH3:10].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:8][C:9]([CH3:11])([CH3:10])[CH2:1][O:2]/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6404Neopentyl alcoholHCID 942973-Buten-2-one, 4-methoxy-

Product 1

HCID 57724954HCID 57724954, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
27.5 °C

Procedure

House vacuum was applied to a mixture of 4-methoxy-3-buten-2-one (14.0 g, 140 mmol) (Fisher Scientific), neopentyl alcohol (18.0 g. 200 mmol), pyrimidium p-toluenesulfonate (0.45 g, 1 mmol) and toluene (50 mL). This was stirred at 25-30° C. for 14 h. All solvent and volatiles were removed by vacuum and the residue was dissolved in hexane (75 mL). This was purified by chromatography (30% ethyl acetate/hexane) to give (E)-4-(2,2-dimethylpropoxy)but-3-en-2-one.

Workup

  1. customAll solvent and volatiles were removed by vacuum
  2. dissolutionthe residue was dissolved in hexane (75 mL)
  3. customThis was purified by chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c53f4920a7bd421f81fa64bc1d4ccd54
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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