Boron trifluoride etherate → Methyl 1-hydroxy-7-methoxynaphthalene-2-carboxylate

HRID 35661노트

반응식

HRID 35661 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15].B(F)(F)F.[CH3:21]COCC>CO>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]([O:16][CH3:21])=[O:15]

참가 물질

4

반응물 2

HCID 8000Boron trifluoride etherateHCID 142567491-Hydroxy-7-methoxynaphthalene-2-carboxylic acid

생성물 1

HCID 13404481Methyl 1-hydroxy-7-methoxynaphthalene-2-carboxylate수율 92.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A suspension of 6.2 g (0.028 mole) of 1-hydroxy-7-methoxy-2-naphthalenecarboxylic acid in 75 ml of methanol under a nitrogen atmosphere was treated over 15 minutes with 15.0 ml (17.3 g; 0.12 mole) of boron trifluoride etherate. The mixture was stirred at reflux for 45 hours, cooled, and added slowly to 500 ml of ice cold 5% aqueous sodium bicarbonate solution. The precipitated product was filtered, and washed with water to yield 6.0 g (92% yield) of the ester, mp 80°-83°, suitable for further synthetic use. A sample purified by chromatography (silica gel, dichloromethane elution) was analytically pure, mp 79°-81° (a mp of 81°-82° is given by M. E. Alonso, A. W. Chitty, S. Pekerar, and M. de L. Borgo, J. Chem. Soc. Chem. Comm., 1542 (1984).

후처리

  1. temperatureat reflux for 45 hours
  2. temperaturecooled
  3. filtrationThe precipitated product was filtered
  4. washwashed with water

출처 및 근거

ORD 기록
ord-d4f8c9d85c0c423a9f6818950109a79c
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767776

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