3-Methyl-2-buten-1-OL → Methyl 3,3-dimethyl-4-pentenoate

HRID 1758562Notes

Reaction equation

HRID 1758562 reaction equation
[C:1](OC)([O:5][CH3:6])([O:3]C)[CH3:2].[CH3:9][C:10]([CH3:14])=[CH:11][CH2:12]O>P(=O)(O)(O)O.CO>[CH3:9][C:10]([CH3:14])([CH:11]=[CH2:12])[CH2:2][C:1]([O:5][CH3:6])=[O:3]

Participants

5

Reactant 2

HCID 111733-Methyl-2-buten-1-OLHCID 15050Trimethyl orthoacetate

Product 1

HCID 114129Methyl 3,3-dimethyl-4-pentenoateYield 63.2%

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of trimethyl orthoacetate (120 g; 1 mole) and orthophosphoric acid (1.5 g; 0.015 mole) was placed in a flask equipped with a stirrer and a 10 cm fractionating column packed with Fenske rings and the mixture was heated, with stirring, to a temperature of 110° C. 3-Methylbut-2-enol (21.5 g; 0.25 mole) was added to the hot reaction mixture over a period of 4 minutes and the methanol formed was collected by distillation over a period of 30 minutes. The excess trimethyl orthoacetate was then distilled from the reaction mixture over a period of 90 minutes. The product was then distilled to give methyl 3,3-dimethylpent-4-enoate (22.4 g; 63.2%), bp 70° C. at 60 mm Hg.

Workup

  1. customwas placed in a flask
  2. customequipped with a stirrer
  3. temperaturethe mixture was heated
  4. distillationwas collected by distillation over a period of 30 minutes
  5. distillationThe excess trimethyl orthoacetate was then distilled from the reaction mixture over a period of 90 minutes
  6. distillationThe product was then distilled

Sources & evidence

ORD record
ord-3bfde84b9461409ea8aedb6c57ce728a
Source dataset
uspto-grants-1983_02
Patent number
US04374264

Reaction notes

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