3-Methyl-2-buten-1-OL → Ethyl 3,3-dimethylpent-4-enoate

HRID 2119081Notes

Reaction equation

HRID 2119081 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4]O.[C:7]([O-:13])([O-])([O:9][CH2:10][CH3:11])[CH3:8]>C1(C=CC(O)=CC=1)O>[CH3:1][C:2]([CH3:6])([CH:3]=[CH2:4])[CH2:8][C:7]([O:9][CH2:10][CH3:11])=[O:13]

Participants

4

Reactant 2

HCID 111733-Methyl-2-buten-1-OLHCID 86598186Ethyl ortho-acetate2×

Product 1

HCID 82262Ethyl 3,3-dimethylpent-4-enoateYield 75.1%

Reagents, catalysts & solvents 1

HCID 785HydroquinoneCatalyst

Procedure

A mixture of 12.9 g (0.15 mole) of 3-methyl-2-buten-1-ol, 48.6 g (0.3 mole) of ethyl orthoacetate and 0.5 g of hydroquinone was heated at 140° for 20 hours with stirring. Ethanol was removed by distillation during the heating. At the end of 20 hours, the mixture was distilled under reduced pressure to give, after removal of unreacted ethyl orthoacetate, 17.6 g (75% yield) of ethyl 3,3-dimethyl-4-pentenoate, b.p. 74°-78°/55 mm.

Workup

  1. temperaturewas heated at 140° for 20 hours
  2. customEthanol was removed by distillation during the heating
  3. distillationAt the end of 20 hours, the mixture was distilled under reduced pressure
  4. customto give

Sources & evidence

ORD record
ord-38170b0f841140b68137d1665f823304
Source dataset
uspto-grants-1987_07
Patent number
US04681953

Reaction notes

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