Water → 2-(p-Isobutylphenyl)propionic acid-p-methoxybenzyl ester

HRID 26450

Reaktionsgleichung

Reaktionsgleichung von HRID 26450
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12](Cl)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][OH:25])=[CH:22][CH:23]=1.C(N(CC)CC)C.O>O1CCCC1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][C:12](=[O:13])[CH:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=2)[CH3:15])=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Produkt 1

HCID 213233092-(p-Isobutylphenyl)propionic acid-p-methoxybenzyl esterAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2.24 g of 2-(p-isobutylphenyl)propionic acid chloride and 2.10 g of p-methoxybenzyl alcohol in 20 ml of tetrahydrofuran was added 1.50 g of triethylamine under cooling and the whole was stirred for 2 hours. After the reaction was complete, an insoluble matter produced was removed by filtration. The solvent was removed from the filtrate by distillation under reduced pressure. To the residue thus obtained was added water and the resulting mixture was extracted with ether. The ether layer separated was washed with successive, 5% sodium carbonate solution, 5% hydrochloric acid solution and water, and then dehydrated. The ether was removed by distillation to give an oily product. Distillation of this product under reduced pressure yielded 2.81 g of 2-(p-isobutylphenyl)propionic acid-p-methoxybenzyl ester as a colorless oil, boiling at 149°-151° C./0.1 mmHg. Analysis-Calculated for C21H26O3 : C, 77.27; H, 8.03. Found: C, 77.11; H, 8.12.

Aufarbeitung

  1. temperatureunder cooling
  2. customan insoluble matter produced
  3. customwas removed by filtration
  4. customThe solvent was removed from the filtrate by distillation under reduced pressure
  5. customTo the residue thus obtained
  6. extractionthe resulting mixture was extracted with ether
  7. customThe ether layer separated
  8. washwas washed with successive, 5% sodium carbonate solution, 5% hydrochloric acid solution and water
  9. customThe ether was removed by distillation
  10. customto give an oily product
  11. distillationDistillation of this product under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b03e21a97e746babc6a047de1e79e96
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04150137

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