Formaldehyde → Benzyl 4-hydroxy-3-hydroxymethylbenzoate

HRID 1729536Notes

Reaction equation

HRID 1729536 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-81fc43ad7b1e49b2bd7f8d3ee0f8d5c7
Source dataset
uspto-grants-1994_07
Patent number
US05332856

Reaction notes

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