Sulfamic Acid → 4-Hydroxy-3-(methoxycarbonyl)benzoic acid

HRID 1623726Notes

Reaction equation

HRID 1623726 reaction equation
S(=O)(=O)(O)N.CC(CC)=C.[CH:11]([C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:12].Cl([O-])=[O:25].[Na+]>O1CCCC1.O.CS(C)=O>[OH:23][C:16]1[CH:15]=[CH:14][C:13]([C:11]([OH:25])=[O:12])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

8

Reactant 4

HCID 5987Sulfamic AcidHCID 112402-Methyl-1-buteneHCID 14363598Methyl 5-FormylsalicylateHCID 23668197Sodium Chlorite

Product 1

HCID 132228014-Hydroxy-3-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sulfamic acid (1.83 g, 18.87 mmol) and 2-methyl-1-butene (1.20 ml, 11.10 mmol) were added to a solution of methyl 5-formyl-2-hydroxybenzoate (may be prepared as described in Description 106; 1 g, 5.55 mmol) in tetrahydrofuran (20 ml), water (20 ml) and dimethyl sulfoxide (20 ml). The solution was cooled to 0° C. and sodium chlorite (1.51 g, 16.65 mmol) in water (5 ml) was added. After 45 minutes at 0° C. the reaction the mixture was quenched with saturated Na2S2O3 solution (20 ml) and extracted with ethyl acetate (3×30 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a solid. 1.09 g (damp with DMSO/H2O).

Workup

  1. customAfter 45 minutes at 0° C. the reaction the mixture
  2. customwas quenched with saturated Na2S2O3 solution (20 ml)
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b0ebfca5855842d084e30d1f92b5a80d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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