3-Methyl-2-buten-1-OL → Ethyl 3,3-dimethylpent-4-enoate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated at 140° for 20 hours
- customEthanol was removed by distillation during the heating
- distillationAt the end of 20 hours, the mixture was distilled under reduced pressure
- customto give
Sources & evidence
- ORD record
- ord-975f344e2ddf41008236f96ee7ec480b
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04999451
Reaction notes
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