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

HRID 1762757Notes

Reaction equation

HRID 1762757 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]>C(O)C>[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-acetate

Product 1

HCID 82262Ethyl 3,3-dimethylpent-4-enoateYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.3 g of 3-methyl-2-buten-1-ol and 8.1 g of ethyl orthoacetate was heated with stirring. The temperature was increased slowly from room temperature to 165° over 2 hours, during which 2.21 g of ethanol was collected. The temperature was maintained at 165° for 26 hours, during which time an additional 1.52 g of ethanol was collected. The reaction mixture was then allowed to cool and diluted with diethyl ether. The ether solution was washed successively with dilute hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The washed solution was dried over magnesium sulfate and distilled to give 4.03 g (52% yield) of ethyl 3,3-dimethyl-4-pentenoate, b.p. 80°-85°/52 mm.

Workup

  1. temperaturewas heated
  2. customwas collected
  3. temperatureThe temperature was maintained at 165° for 26 hours, during which time an additional 1.52 g of ethanol
  4. customwas collected
  5. temperatureto cool
  6. additiondiluted with diethyl ether
  7. washThe ether solution was washed successively with dilute hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  8. dry with materialThe washed solution was dried over magnesium sulfate
  9. distillationdistilled

Sources & evidence

ORD record
ord-2405a0c838144f289e88b58a10e4a2d9
Source dataset
uspto-grants-1989_05
Patent number
US04833266

Reaction notes

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