Hydrochloric Acid → 5-(1,1-Dimethylethyl)salicylic acid

HRID 644403Notes

Reaction equation

HRID 644403 reaction equation
S(=O)(=O)(O)N.P([O-])(O)(O)=O.[Na+].[CH3:12][C:13]([C:16]1[CH:17]=[CH:18][C:19]([OH:24])=[C:20]([CH:23]=1)[CH:21]=[O:22])([CH3:15])[CH3:14].Cl([O-])=[O:26].[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[CH3:15][C:13]([C:16]1[CH:23]=[C:20]([C:21]([OH:26])=[O:22])[C:19]([OH:24])=[CH:18][CH:17]=1)([CH3:12])[CH3:14]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 24437Sodium SulfiteHCID 14750905-tert-ButylsalicylaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 852815-(1,1-Dimethylethyl)salicylic acidYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

Sulfamic acid (1.76 g, 18.1 mmol) and sodium dihydrogenphosphate (7.33 g, 47 mmol) were added to a solution of 5-[(1,1-dimethyl)ethyl]-2-hydroxybenzaldehyde (2.15 g, 12.1 mmol) in 1,4-dioxane (100 mL) and water (40 mL). A solution of sodium chlorite (1.76 g, 15.5 mmol) in water (10 mL) was added to the mixture under ice cooling, and it was stirred for 1 hour. Then, sodium sulfite (1.80 g, 14.3 mmol) was added to the mixture, and it was stirred for 30 minutes. Concentrated hydrochloric acid was added to the reaction mixture, and pH was adjusted to 1. The residue obtained by evaporation of 1,4-dioxane under reduced pressure was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was washed with n-hexane under suspension to give the title compound (1.81 g, 77.4%) as a white powder.

Workup

  1. stirringwas stirred for 30 minutes
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. washwas washed with n-hexane under suspension

Sources & evidence

ORD record
ord-2264af9ccfcd423fa411b486b2d2147d
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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