Ethanol → 2,2-Dimethyl-4-pentenoic acid

HRID 969751Notes

Reaction equation

HRID 969751 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:12][CH:13]=[CH2:14])[C:3]([O:5][Si](OCC)(C)C)=[O:4].C(O)C>>[CH3:1][C:2]([CH3:15])([CH2:12][CH:13]=[CH2:14])[C:3]([OH:5])=[O:4]

Participants

3

Reactant 2

HCID 702EthanolHCID 86039065HCID 86039065, compound

Product 1

HCID 1400652,2-Dimethyl-4-pentenoic acidYield 93.4%

Procedure

A 100-ml four-necked flask equipped with a Dimroth reflux condenser, stirrer and thermometer was purged with nitrogen. The flask was charged with 17.7 g (0.0768 mol) of ethoxydimethylsilyl 2,2-dimethyl-4-pentenoate and 14.2 g (0.307 mol) of ethanol. The contents were stirred at room temperature for one hour, then at 60-65° C. for 5 hours. The reaction mixture was vacuum distilled, collecting 9.2 g of a colorless clear fraction having a boiling point of 78-79° C./0.6 kPa. On NMR and GC/MS analysis, the liquid was identified to be the target compound, 2,2-dimethyl-4-pentenoic acid. The yield was 93.4%. 1H-NMR (CDCl3, 300 MHz): δ (ppm) 11.9 (1H, br), 5.84-5.70 (1H, m), 5.11-5.08 (1H, m), 5.07-5.04 (1H, m), 2.30 (2H, dt, J=7.3 Hz, 1.1 Hz), 1.19 (6H, s) 13C-NMR (CDCl3, 75.6 MHz): δ (ppm) 184.6, 133.9, 118.2, 44.4, 42.2, 24.5 MS (EI): m/z 128 (M+), 113, 83, 55, 41

Workup

  1. customA 100-ml four-necked flask equipped with a Dimroth
  2. temperaturereflux condenser, stirrer
  3. customthermometer was purged with nitrogen
  4. waitat 60-65° C. for 5 hours
  5. distillationdistilled
  6. customcollecting 9.2 g of a colorless clear fraction

Sources & evidence

ORD record
ord-12aca79dda8144b8ab125afaa82c4faa
Source dataset
uspto-grants-2007_12
Patent number
US07307178B2

Reaction notes

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