Formaldehyde → Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

HRID 1656564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656564
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]=[O:15])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:16]=[O:17].[Br-].C(C1SC2C=CC=CC=2[NH+]=1)C.C(N(CC)CC)C>C(O)C>[OH:17][CH2:16][C:14](=[O:15])[CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 2757377Ethyl 4-(3-oxopropyl)benzoateHCID 68772949Ethyl benzothiazolium bromide

Produkt 1

HCID 10609833Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.1 g (5 mmol) of 3-(4-carbethoxyphenyl)propanal and 150 mg (5 mmol) of paraformaldehyde in 10 mL of ethanol, together with 230 mg (0.9 mmol) of ethyl benzothiazolium bromide and 90 mg (0.9 mmol) of triethylamine, is heated at about 70° C. for 16 hours. The reaction mixture is concentrated in vacuo and the product further purified by chromatography on silica gel, eluting with 15:85 ethyl acetate:hexane, to yield ethyl 4-(4-hydroxy-3-oxobutyl)benzoate as a colorless oil which solidifies upon standing; m.p. 51°-52° C. Anal. calcd for C13H16O4 : C, 66.09; H 6.83. Found: C, 66.29; H, 6.70.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe product further purified by chromatography on silica gel
  3. washeluting with 15:85 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b84a1bc7fcda459b8fc671faf878f9be
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254687

Notizen zur Reaktion

Wird geladen…