Water → Methyl 5-Formylsalicylate

HRID 1623725Notes

Reaction equation

HRID 1623725 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].OS(O)(=O)=O.[CH2:18](Cl)Cl.O>CO>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([O:10][CH3:18])=[O:9])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 692265-Formylsalicylic acid

Product 1

HCID 14363598Methyl 5-Formylsalicylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-formyl-2-hydroxybenzoic acid (3 g, 18.06 mmol) in methanol (10 ml) was added H2SO4 (0.5 ml, 9.38 mmol). The solution was heated at 50° C. for 18 hours. The solution was cooled, and DCM (30 ml) and water (20 ml) were added. The organic layer was separated, washed with NaHCO3 (10 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a yellow solid. 3.1 g.

Workup

  1. temperatureThe solution was cooled
  2. customThe organic layer was separated
  3. washwashed with NaHCO3 (10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8434dec60c6945bbb227e163bf38b303
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…