Pyridine → 2-Methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester

HRID 277580

Reaction equation

HRID 277580 reaction equation
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[S:17](Cl)(=[O:19])=[O:18].N1C=CC=CC=1.O1CCOCC1>C(OCC)(=O)C>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[S:17]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6404Neopentyl alcoholHCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 312751,4-Dioxane

Product 1

HCID 571129482-Methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl esterYield 57.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Neopentyl alcohol (0.75 g, 8.50 mmol) was added to a solution of commercially available 2-methyl-5-nitro-benzenesulfonyl chloride (1.00 g, 4.20 mmol), pyridine (1.72 mL, 21.2 mmol and anhydrous dioxane (40 mL). A water cooled condenser was attached and the material was heated to reflux. After stirring for two days the mixture was cooled to room temperature and diluted with ethyl acetate (350 mL). The organic layer was washed with water, then 1 N HCl solution, and finally brine. After drying with MgSO4 the solution was concentrated to afford 690 mg of the title compound as a yellow solid.(55%): 1HNMR (DMSO-6) δ8.57 (d, J=2 Hz, 1H), 8.51 (dd, J=8 Hz, 2 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 3.78 (s, 2H), 2.70 (s, 3H), 0.88 (s, 9H); MS (EI): [M+] 287; Anal. Calc. for C12H17NO5S: C, 50.16; H, 5.96; N, 4.88. Found: C, 49.83; H, 5.69; N, 4.90.

Workup

  1. customA water cooled condenser was attached
  2. temperaturethe material was heated to reflux
  3. washThe organic layer was washed with water
  4. dry with materialAfter drying with MgSO4 the solution
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-73b32ef307804d0996e14009bb4be59c
Source dataset
uspto-grants-2002_03
Patent number
US06355633B1

Linked notes

Loading…