Potassium tert-butoxide → 4-(Cyclopropylsulfonyl)benzoic acid

HRID 73008Notes

Reaction equation

HRID 73008 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)(=[O:7])=[O:6].CC(C)([O-])C.[K+]>CC(O)(C)C.O>[CH:4]1([S:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68290846Methyl 4-(3-chloropropylsulfonyl)benzoate

Product 1

HCID 674685354-(Cyclopropylsulfonyl)benzoic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-(3-chloropropylsulfonyl)benzoate (1.89 g, 6.83 mmol) in 2-methylpropan-2-ol (20 mL) was added potassium tert-butoxide (1.53 g, 13.7 mmol) and the slurry heated at 80° C. for 10 min. Additional 2-methylpropan-2-ol (20 mL) was added to facilitate stirring and the heating continued for 25 min. The reaction mixture was diluted with water (100 mL) and washed with ethyl acetate (3×100 mL). The aqueous layer was acidified with 1N HCl and extracted with ethyl acetate (3×100 mL). The combined organics were dried over Na2SO4, filtered and the solvent removed in vacuo to provide 4-cyclopropylsulfonylbenzoic acid (1.22 g, 79%) as a beige solid. ESI-MS m/z calc. 226.0. Found 227.3 (M+1)+; Retention time: 0.86 minutes (3 min run).

Workup

  1. washwashed with ethyl acetate (3×100 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d3b96ad4816842d48676b7650cdf1b00
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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