Sodium Chloride → Hydrochloric Acid

HRID 888400Notes

Reaction equation

HRID 888400 reaction equation
[Cl-:1].[Na+].[C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:14]=1)[C:9]([OH:11])=[O:10])([CH3:5])=[CH2:4].CS(O)(=O)=[O:24].[OH-].[Na+]>O>[ClH:1].[OH:24][C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:14]=1)[C:9]([OH:11])=[O:10])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 684948073-Isopropenyl-5-(5-methylpyridin-2-yl)benzoic acid

Product 2

HCID 313Hydrochloric AcidHCID 685016863-(1-Hydroxy-1-methylethyl)-5-(5-methylpyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the sodium chloride salt of 3-isopropenyl-5-(5-methylpyridin-2-yl)benzoic acid (2.114 g, 4.93 mmol) in water (49.3 mL) at 0° C. was added methanesulfonic acid (23.7 mL, 247 mmol) and the mixture was heated to 50° C. After 16 h, the mixture was cooled to 0° C. and sodium hydroxide (9.86 g, 247 mmol) added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→65% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrochloric acid in diethyl ether gave the title compound as a hydrochloride salt (1.252 g). MS 272.0 (M+1).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→65% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-85115ba3c7fd496f9f7f27ed5937d2e6
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

Loading…