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

HRID 359164

Reaction equation

HRID 359164 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-975f344e2ddf41008236f96ee7ec480b
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Linked notes

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