Water → 6-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid

HRID 2393187

Reaktionsgleichung

Reaktionsgleichung von HRID 2393187
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[C:22]1(O)[CH:27]=CC=[CH:24][CH:23]=1.B(F)(F)F.C[CH2:34][O:35][CH2:36][CH3:37].[OH2:38]>ClCCl>[CH3:34][O:35][C:36]1[CH:37]=[CH:24][C:23]([CH:14]([C:4]2[C:3](=[O:2])[C:12]3[C:7]([C:6](=[O:38])[C:5]=2[CH3:13])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:22][CH:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 996PhenolHCID 8000Boron trifluoride etherateHCID 542608176-(1-Methoxy-3-methylnaphth-2-yl)-5-hexenoic acid

Produkt 1

HCID 152308586-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a solution of 6-(1-methoxy-3-methylnaphth-2-yl)-5-hexenoic acid (70 g) and phenol (70 g) in dichloromethane (500 ml) was added boron trifluoride etherate (95 g) and the reaction mixture was stirred for 3 days at 35° C. and poured into cooled water. The organic layer was washed with water, dried, and evaporated. The residue was purified with silica gel chromatography (eluent; toluene, 20% ethyl acetate/hexane, and ethyl acetate) to give the titled compound (30 g).

Aufarbeitung

  1. additionpoured
  2. washThe organic layer was washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was purified with silica gel chromatography (eluent; toluene, 20% ethyl acetate/hexane, and ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1470db528db146f7b88e40d64e826c39
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804601

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