Sulfuric Acid → Naproxen

HRID 1585244Notes

Reaction equation

HRID 1585244 reaction equation
[Na].[CH3:2][C@H:3]([C:16]([OH:18])=[O:17])[C:4]1[CH:5]=[CH:6][C:7]2[CH:8]=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][C:12]=2[CH:13]=1.S(=O)(=O)(O)O>>[CH3:2][C@H:3]([C:16]([OH:18])=[O:17])[C:4]1[CH:5]=[CH:6][C:7]2[CH:8]=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][C:12]=2[CH:13]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 9837916Sodium naproxen2×

Product 1

HCID 156391Naproxen

Conditions

Temperature
92 °C

Procedure

A total of 6029.3 gm of an aqueous solution of sodium naproxen, prepared in accordance with the procedure of Example 1 and having 19.05 wt % sodium naproxen and a S(+)-isomer chiral purity of 97.81%, is heated to and maintained at 92° C. To this solution, 665.73 gm of dilute (30.88 wt %) sulfuric acid was fed continuously over 95 minutes. The resulting slurry was aged at 89° C. for 30 minutes and cooled to 80° C. in 30 minutes. The product was isolated using a basket centrifuge, washed with 5837 gm of hot (80° C.) water, and dried under vacuum in an oven at 90° C. A total of 993.84 gm of dry free acid naproxen final product was obtained and determined to have a chiral purity of 99.03% in the S(+)-isomer form.

Workup

  1. waitThe resulting slurry was aged at 89° C. for 30 minutes
  2. temperaturecooled to 80° C. in 30 minutes
  3. customThe product was isolated
  4. washwashed with 5837 gm of hot (80° C.) water
  5. customdried under vacuum in an oven at 90° C

Sources & evidence

ORD record
ord-33690bca403b4b5d82d122ea5d56ae8e
Source dataset
uspto-grants-1999_08
Patent number
US05936118

Reaction notes

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