Ethanol → Benzoic acid, 3,5-dihydroxy-, ethyl ester

HRID 596553

Reaction equation

HRID 596553 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[OH:5][C:4]1[CH:3]=[C:2]([CH:9]=[C:7]([OH:8])[CH:6]=1)[C:1]([O:11][CH2:17][CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74243,5-Dihydroxybenzoic Acid

Product 1

HCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl ester

Procedure

308 g. of α-resorcylic acid were dissolved in 1000 ml of absolute ethanol and 25 ml of concentrated sulphuric acid were added. The reaction mixture was boiled under reflux for 20 hours. The ethanol was evaporated and the residue poured into water and extracted with ether. The etheral phase was washed with sodium bicarbonate solution and water and dried with magnesium sulphate. When the ether was evaporated, a crystallizing residue was obtained.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe ethanol was evaporated
  3. additionthe residue poured into water
  4. extractionextracted with ether
  5. washThe etheral phase was washed with sodium bicarbonate solution and water
  6. dry with materialdried with magnesium sulphate
  7. customWhen the ether was evaporated
  8. customa crystallizing residue was obtained

Sources & evidence

ORD record
ord-e25275f85899497b949fae76d595567b
Source dataset
uspto-grants-1977_03
Patent number
US04011258

Linked notes

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