Water → Methyl 5-Formylsalicylate

HRID 1663376Notes

Reaction equation

HRID 1663376 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:2].S(=O)(=O)(O)O.[CH2:18](OCC)C.O>CO>[CH3:18][O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([CH:1]=[O:2])[CH:4]=[CH:5][C:6]=1[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 692265-Formylsalicylic acid

Product 1

HCID 14363598Methyl 5-Formylsalicylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Formyl-2-hydroxy-benzoic acid (11.3 g) was dissolved in methanol (35 ml) and conc. sulfuric acid (3 ml). The mixture was heated at reflux for 40 h. Diethyl ether was added, and the mixture was poured into water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in a mixture of dioxane (80 ml) and water (50 ml) and treated with 6N hydrochloric acid (2.5 ml). After 15 min., dioxane was removed in vacuo. The mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 40 h
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in a mixture of dioxane (80 ml) and water (50 ml)
  7. additiontreated with 6N hydrochloric acid (2.5 ml)
  8. customdioxane was removed in vacuo
  9. extractionThe mixture was extracted with ethyl acetate
  10. dry with materialThe organic layer was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91de6c18800d459eb1917f4e77f5d63b
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

Loading…