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

HRID 1018708Notes

Reaction equation

HRID 1018708 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): δ 1.28 (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-4beb74cebe5a4f4db7c4f066df71decb
Source dataset
uspto-grants-2002_11
Patent number
US06482907B1

Reaction notes

Loading…