Ethanol → 5-(Benzyloxy)-2-hydroxybenzaldehyde

HRID 466170ノート

反応式

HRID 466170 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)(Cl)Cl.[CH2:22]([OH:24])C>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[C:13]([CH:14]=1)[CH:22]=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 702EthanolHCID 6212ChloroformHCID 7638MonobenzoneHCID 14798Sodium Hydroxide

生成物 1

HCID 8783625-(Benzyloxy)-2-hydroxybenzaldehyde

反応条件

温度
70 °C

実験手順

The starting material is prepared as follows: 4-Benzyloxyphenol (20 g, 0.1 mol) is dissolved in 24 ml of ethanol and 120 ml of 20% aqueous sodium hydroxide (24 g NaOH, 0.6 mol), and heated at 70° C. To this is added chloroform (23.9 g, 0.2 mol) dropwise and the mixture is stirred for 3.5 hours at 70° C. The mixture is cooled and evaporated. The residue is then treated with conc. HCl until the pH of the solution is 1 to 3. The mixture is extracted with ether three times, and the combined organic layer is dried (MgSO4), evaporated and purified by silica gel chromatography (5% ethyl acetate/hexane) to give 5-benzyloxy-2-hydroxybenzaldehyde as a pale yellow, crystalline solid, m.p. 94°-96° C.

後処理

  1. customThe starting material is prepared
  2. temperatureThe mixture is cooled
  3. customevaporated
  4. additionThe residue is then treated with conc. HCl until the pH of the solution
  5. extractionThe mixture is extracted with ether three times
  6. dry with materialthe combined organic layer is dried (MgSO4)
  7. customevaporated
  8. custompurified by silica gel chromatography (5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-d8376cd991ed4be19b732944861ad40c
出典データセット
uspto-grants-1992_10
特許番号
US05155130

反応ノート

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