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

HRID 1762754Notes

Reaction equation

HRID 1762754 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-b50acdb2f71745b5ac3faf66771c0d64
Source dataset
uspto-grants-1989_05
Patent number
US04833266

Reaction notes

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