Hydrochloric Acid → 4-(MethanesulfonylMethyl)benzoic acid

HRID 277578Notes

Reaction equation

HRID 277578 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].Cl>[OH-].[Na+]>[CH3:1][S:2]([CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2804364methyl 4-(methylsulfonylmethyl)benzoate

Product 1

HCID 5060694-(MethanesulfonylMethyl)benzoic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of commercially available methyl 4-(methanesulphonylmethyl)benzoate (1.00 g, 4.4 mmol) in 2M NaOH (25 mL) was heated at reflux for 30 minutes under N2. The reaction mixture was cooled to 0° C. and acidified with 2M HCl (15 mL) to a pH below 2. The white precipitate was filtered and dried to provide the title compound as a white solid (0.95 g, 97% yield): 1HNMR (DMSO-d6) δ2.97 (s, 3H), 4.61 (s, 2H), 7.49 (d, J=0.5 Hz, 2H), 7.94-7.98 (d, J=0.5 Hz, 2H), 13.00 (s, 1H): MS (ESI) [M−H]− at m/z 213.

Workup

  1. temperatureat reflux for 30 minutes under N2
  2. filtrationThe white precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-707bf3a60b254a74ab61480452a90733
Source dataset
uspto-grants-2002_03
Patent number
US06355633B1

Reaction notes

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