Sulfamic Acid → 4-Phenoxybenzoic acid

HRID 1178022Notes

Reaction equation

HRID 1178022 reaction equation
S(=O)(=O)(O)N.[O:6]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl([O-])=[O:22].[Na+]>O.CC(C)=O>[O:6]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:22])=[O:18])=[CH:19][CH:20]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 661394-PhenoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 751824-Phenoxybenzoic acidYield 74%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

Sulfamic acid (7.35 g, 75.7 mmol) in water (5 mL) was added to a stirred solution of 4-phenoxy benzaldehyde (5 g, 25.23 mmol) in acetone (25 mL) at 4° C. Sodium chlorite (9.13 g, 100.9 mmol) in water (5 mL) was then added slowly resulting in formation of a yellow solid with effervescence. The mixture was stirred at the same temperature for 30 minutes. The reaction mixture was then diluted with cold water and the product extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 4 g (74% yield) of 4-phenoxy benzoic acid. 1H NMR (DMSO): δ 7.98-7.92 (d, 2H), 7.5-7.44 (t, 2H), 7.28-7.2 (t, 1H), 7.16-7.1 (d, 2H), 7.06-7.0 (d, 2H).

Workup

  1. customresulting in formation of a yellow solid with effervescence
  2. extractionthe product extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a5a4cac6d8b4c8eabfb5dd9d5087899
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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