Hydrogen Bromide → 7-Hydroxy-2-naphthoic acid

HRID 1640111ノート

反応式

HRID 1640111 の反応式
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]([O:15]C)=[O:14])=[CH:10]2)=[CH:5][CH:4]=1.Br>CC(O)=O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10]2)=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 10082020Methyl 7-methoxynaphthalene-2-carboxylate

生成物 1

HCID 145125257-Hydroxy-2-naphthoic acid収率 99.8%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A suspension of methyl 7-methoxy-2-naphthoate (37.21 g, 172 mmol) in 48% aqueous HBr (195 mL, 1.72 mol) and AcOH (190 mL) was heated at 100° C. for 4 h. The mixture gradually went into solution and then precipitated. The reaction mixture was cooled to rt, and water was added. The solid was filtered and washed with water. The solid was dissolved in 1N NaOH and washed with Et2O. The aqueous solution was acidified to pH 1 with concentrated HCl. The precipitate was filtered and washed with water, then dried under vacuum to give 7-hydroxy-2-naphthoic acid as an off-white solid (32.3 g, 99%). LCMS: (FA) ES− 187.1.

後処理

  1. customprecipitated
  2. temperatureThe reaction mixture was cooled to rt
  3. additionwater was added
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. dissolutionThe solid was dissolved in 1N NaOH
  7. washwashed with Et2O
  8. filtrationThe precipitate was filtered
  9. washwashed with water
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-79a85e264a444954bbcdb2999b691693
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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