Phenol → Ethyl 3,3-dimethylpent-4-enoate

HRID 2119082Notes

Reaction equation

HRID 2119082 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(O)C=CC=CC=1>>[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 3

HCID 996PhenolHCID 111733-Methyl-2-buten-1-OLHCID 86598186Ethyl ortho-acetate

Product 1

HCID 82262Ethyl 3,3-dimethylpent-4-enoateYield 78%

Procedure

A mixture of 43 g (0.5 mole) of 3-methyl-2-buten-1-ol, 97 g (0.6 mole) of ethyl orthoacetate, and 7.0 g (0.075 mole) of phenol was heated at 135°-140° with stirring for 9-10 hours. Ethanol was distilled from the mixture as the reaction proceeded. When the evolution of ethanol had ceased, heating was discontinued and the mixture was allowed to cool to room temperature. The mixture was then dissolved in diethyl ether and the ethereal solution was treated with IN hydrochloric acid to decompose unreacted ethyl orthoacetate. The ethereal solution was then washed successively with a saturated aqueous solution of sodium bicarbonate and with water, then dried over magnesium sulfate. The dried solution was concentrated and distilled under reduced pressure to give 60.8 g (78% yield) of ethyl 3,3-dimethyl-4-pentenoate, b.p. 57°-60°/11 mm.

Workup

  1. temperaturewas heated at 135°-140°
  2. distillationEthanol was distilled from the mixture as the reaction
  3. temperatureheating
  4. dissolutionThe mixture was then dissolved in diethyl ether
  5. additionthe ethereal solution was treated with IN hydrochloric acid
  6. washThe ethereal solution was then washed successively with a saturated aqueous solution of sodium bicarbonate and with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe dried solution was concentrated
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-a00e41c076d94f909982867e03cd4693
Source dataset
uspto-grants-1987_07
Patent number
US04681953

Reaction notes

Loading…