Acetic Acid → 2',3'-Dihydroxyacetophenone

HRID 38628

Reaktionsgleichung

Reaktionsgleichung von HRID 38628
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[C:9](O)(=[O:11])[CH3:10].B(F)(F)F>CCOCC>[CH3:10][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:1]([OH:2])[C:3]=1[OH:4])=[O:11]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 289CatecholHCID 6356Boron trifluoride

Produkt 1

HCID 64291102',3'-Dihydroxyacetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

6-Amino-2,3-dimethoxyacetophenone (2) was also prepared according to published methods. The starting catechol (28) was acetylated, in microwave oven set at 300 Watt power, by reacting with mixture of acetic acid (29) and BF3. Et2O to yield 2,3-dihydroxyacetophenone (30) which was further reacted with diiodomethane in DMF, in the presence of K2CO3, to afford 2,3-methylenedioxyacetophenone (31). Subsequent nitration of compound 31 with 70% HNO3 afforded 2,3-methylenedioxy-6-nitroacetophenone (32). Without purification, compounds 32 was hydrogenated, and purified with column chromatography to provide 6-amino-2,3-methylenedioxyacetophenone (2).10 Another published method was followed in preparation of 6-amino-3-methoxy-4-benzyloxyacetophenone (3). First, the benzylation of the starting acetovanillone (33) with benzylbromide (34) gave 4-benzyloxy-3-methoxyacetophenone (35) which was nitrated to yield 4-benzyloxy-3-methoxy-6-nitroacetophenone (36).11 The so-obtained compound 36 was reduced with SnCl2 to afford compound 3.

Quellen und Nachweise

ORD-Eintrag
ord-a90466c8353941d38fddfb07bee5af59
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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