Formaldehyde → Benzyl 4-hydroxy-3-hydroxymethylbenzoate

HRID 129676

반응식

HRID 129676 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 19372223Benzyl 4-hydroxy-3-hydroxymethylbenzoate수율 287.2%

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc764d4caba24ff4bb41abc4b7299f25
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468897

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