Methanol → Methyl 2,2-dimethylpent-4-enoate

HRID 395897

Reaction equation

HRID 395897 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=[CH2:8])[C:3]([OH:5])=[O:4].[CH3:10]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=[CH2:8])[C:3]([O:5][CH3:10])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1400652,2-Dimethyl-4-pentenoic acid

Product 1

HCID 11768679Methyl 2,2-dimethylpent-4-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,2-Dimethyl-4-pentenoic acid (15 g, 0.117 mol) was mixed with 70 mL anhydrous methanol and 50 mL toluene. Concentrated sulfuric acid (0.1 mL) was added. The solution was refluxed for 24 h. Solvents were then removed. The crude product was distilled under reduced pressure to gave 6 g pure product. 1H NMR(CDCl3) δ1.28(s, 6H, —CMe2—); 2.37(d, 2H, CH2═CHCH2—); 3.77(s, 3H, —CO2Me); 5.15(m, 2H, CH2═CH—); 5.84(m, 1H, CH2═CH—)

Workup

  1. temperatureThe solution was refluxed for 24 h
  2. customSolvents were then removed
  3. distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-b28d5c9c0660451397b170954272443c
Source dataset
uspto-grants-2003_08
Patent number
US06605679B1

Linked notes

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