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

HRID 35661ノート

反応式

HRID 35661 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 13404481Methyl 1-hydroxy-7-methoxynaphthalene-2-carboxylate収率 92.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-d4f8c9d85c0c423a9f6818950109a79c
出典データセット
uspto-grants-1988_08
特許番号
US04767776

反応ノート

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