Methanol → Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

HRID 1883212Notes

Reaction equation

HRID 1883212 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:16]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 94475-Chlorosalicylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterYield 74%

Conditions

Temperature
60 °C

Procedure

Under nitrogen atmosphere, a solution of 5-chlorosalicylic acid (5.00 g) in MeOH (100 mL) was cooled to 0° C., and thereto was added dropwise SOCl2 (3.20 mL). After the addition, the mixture was stirred at 60° C. for 10 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, washed twice with water, washed with a saturated brine, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=5/1) to give methyl 5-chloro-2-hydroxybenzoate (4.03 g, 74%).

Workup

  1. additionAfter the addition
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed twice with water
  5. washwashed with a saturated brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-0607485f4b4a491883e298cda189db2f
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

Loading…