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

HRID 1263017

Reaktionsgleichung

Reaktionsgleichung von HRID 1263017
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 13305232(3-Phenoxyphenyl)methyl 3,3-dimethylpent-4-enoateAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8433489b2880451cb163244613d352f0
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04454343

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