Acetic Acid → 2',3'-Dihydroxyacetophenone

HRID 38628

반응식

HRID 38628 반응식
[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]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 289CatecholHCID 6356Boron trifluoride

생성물 1

HCID 64291102',3'-Dihydroxyacetophenone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-a90466c8353941d38fddfb07bee5af59
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524740B2

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