Sulfuric Acid → Tert-butyl 4-hydroxy-3-nitrobenzoate

HRID 1007141Notes

Reaction equation

HRID 1007141 reaction equation
[O-]S([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[OH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].[C:25](O)([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])O.[Na+]>ClCCl>[OH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 120334-Hydroxy-3-nitrobenzoic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 22667857Tert-butyl 4-hydroxy-3-nitrobenzoateYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Magnesium sulfate anhydrous (9.62 g, 80 mmol) was suspended at room temperature in dichloromethane (50 mL) and 96% sulfuric acid (1.1 mL, 20 mmol) was added, the mixture was vigorously stirred for 15 min and then 4-hydroxy-3-nitrobenzoic acid (3.7 g, 20.22 mmol) and tert-butanol (9.6 mL, 100 mmol) were added. Stirring was continued for 48 hours. A saturated sodium hydrogen carbonate solution (150 mL) was slowly added and the mixture was diluted with dichloromethane (150 mL). The organic layer was separated and dried (Na2SO4), evaporated to afford tert-butyl 4-hydroxy-3-nitrobenzoate as a yellow solid (4.43 g, 90%).

Workup

  1. stirringStirring
  2. waitwas continued for 48 hours
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d263270f89c448eaad9b82708e1f9a09
Source dataset
uspto-grants-2004_09
Patent number
US06794385B2

Reaction notes

Loading…