Formaldehyde → Benzyl 4-hydroxy-3-hydroxymethylbenzoate

HRID 129676

反応式

HRID 129676 の反応式
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C1(B(O)O)C=CC=CC=1.C=O.[C:29](O)(=[O:32])CC>C1C=CC=CC=1.O>[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][C:3]=1[CH2:29][OH:32]

参加物

7

反応物 4

HCID 712FormaldehydeHCID 1032Propionic AcidHCID 7180Benzyl 4-HydroxybenzoateHCID 66827Phenylboronic Acid

生成物 1

HCID 19372223Benzyl 4-hydroxy-3-hydroxymethylbenzoate収率 287.2%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

A solution of 27.4 g (0.12 mole) of benzyl 4-hydroxybenzoate, 14.7 g (0.12 mole) of benzeneboronic acid, 6 g (0.135 mole) of paraformaldehyde and 0.9 ml (12 mmoles) of propionic acid in 600 ml of anhydrous benzene is heated at reflux for 12 hours using a Dean-Stark reactor to separate the water formed. The reaction medium is poured into bicarbonated water and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column eluted with dichloromethane. After evaporation of the solvent, 8.9 g (30% yield) of the expected product having a melting point of 109°-110° C. are obtained.

後処理

  1. temperatureat reflux for 12 hours
  2. customto separate the water
  3. customformed
  4. extractionextracted with ethyl ether
  5. customThe organic phase is decanted
  6. washwashed with water
  7. customdried on magnesium sulfate
  8. customevaporated
  9. customThe resulting residue is purified by chromatography on a silica column
  10. washeluted with dichloromethane

出典と根拠

ORDレコード
ord-fc764d4caba24ff4bb41abc4b7299f25
出典データセット
uspto-grants-1995_11
特許番号
US05468897

関連ノート

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