3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester

HRID 2112438

Reaktionsgleichung

Reaktionsgleichung von HRID 2112438
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1.C(Br)(Br)(Br)[Br:21]>>[Br:21][CH2:17][CH2:16][CH2:15][CH2:19][O:11][C:10](=[O:12])[CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=1

Komponenten

4

Edukt 3

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic AcidHCID 8028TetrahydrofuranHCID 11205Carbon tetrabromide

Produkt 1

HCID 539389163-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl esterAusbeute 265,4 %

Versuchsvorschrift

To a solution of 3- (4-hydroxy-3-methoxyphenyl) -2-propenoic acid (10 g, 51.5 mmoles) in THF (400 ml) triphenylphosphine (2.7 g, 10.3 mmoles) and carbon tetrabromide (34.16 g, 10.3 mmoles) are added and the solution is left at room temperature, under magnetic stirring, for 48 hours. The solid is filtered and then evaporated at reduced pressure. The obtained crude product is purified by chromatogrphy on silica gel eluting with n-hexane/ethyl acetate 7/3. 9 g of 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-bromobutyl ester are obtained. M.p.=86-89° C.

Aufarbeitung

  1. filtrationThe solid is filtered
  2. customevaporated at reduced pressure
  3. customThe obtained crude product
  4. customis purified by chromatogrphy on silica gel eluting with n-hexane/ethyl acetate 7/3

Quellen und Nachweise

ORD-Eintrag
ord-0bf0c2072d8f452d81e003b7d4279ad3
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07524836B2

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