3-Phenoxybenzyl alcohol → (3-Phenoxyphenyl)methyl 3,3-dimethylpent-4-enoate

HRID 2119080Notes

Reaction equation

HRID 2119080 reaction equation
[CH3:1][C:2]([CH3:11])([CH:9]=[CH2:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O:12]([C:19]1[CH:20]=C([CH:24]=[CH:25][CH:26]=1)CO)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]CC.[Na+]>C1(C)C=CC=CC=1>[CH3:11][C:2]([CH3:1])([CH:9]=[CH2:10])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:24]=[CH:25][CH:26]=[C:19]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:20]=1)=[O:5]

Participants

5

Reactant 3

HCID 262953-Phenoxybenzyl alcoholHCID 82262Ethyl 3,3-dimethylpent-4-enoateHCID 2723922Sodium ethoxide

Product 1

HCID 13305232(3-Phenoxyphenyl)methyl 3,3-dimethylpent-4-enoateYield 83.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 374 mg of ethyl 3,3-dimethyl-4-pentenoate, 400 mg of 3-phenoxybenzyl alcohol and 16 mg of sodium ethoxide in 10 ml of toluene was heated under reflux for 24 hours, with a Dean-Stark apparatus containing a molecular sieve to absorb the evolved ethanol. The mixture was neutralized by adding an anhydrous ether solution of hydrogen chloride. The neutral solution was poured into water. The ether layer was separated, dried over magnesium sulfate, and distilled to give 520 mg (70% yield) of 3-phenoxybenzyl 3,3-dimethyl-4-pentenoate, b.p. 155°-158°/0.3 mm.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours, with a Dean-Stark apparatus
  3. additioncontaining a molecular sieve
  4. customto absorb the evolved ethanol
  5. additionby adding an anhydrous ether solution of hydrogen chloride
  6. additionThe neutral solution was poured into water
  7. customThe ether layer was separated
  8. dry with materialdried over magnesium sulfate
  9. distillationdistilled

Sources & evidence

ORD record
ord-6e6888fd156c40d1ae85171e9854b146
Source dataset
uspto-grants-1987_07
Patent number
US04681953

Reaction notes

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