Chlorosulfonic acid → Toluene methanol

HRID 1964803Notes

Reaction equation

HRID 1964803 reaction equation
[CH3:1][O:2]C(=O)[C:4](C)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.ClS(O)(=O)=O>C(Cl)Cl>[C:6]1([CH3:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:1][OH:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 143498Methyl 2-methyl-2-phenylpropanoate

Product 1

HCID 21867641Toluene methanolYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-methyl-2-phenyl propanoic methyl ester (1.1 g, 6.17 mmol) was dissolved in 20 mL of anhydrous DCM and the reaction mixture was cooled down to −78° C. The chlorosulfonic acid (2.05 mL, 30.86 mmol, 5 eq) dissolved in 10 mL of anhydrous DCM was added dropwise during a period of 2 h. The reaction mixture was stirred overnight at room temperature. The reaction was quenched by addition of ice and the product extracted with DCM (3×50 mL) The organic layer was washed with NaCl sat, dried over MgSO4, evaporated to give an oil (1 g, yield: 59%, HPLC purity: 84%)

Workup

  1. additionwas added dropwise during a period of 2 h
  2. customThe reaction was quenched by addition of ice
  3. extractionthe product extracted with DCM (3×50 mL) The organic layer
  4. washwas washed with NaCl
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto give an oil (1 g, yield: 59%, HPLC purity: 84%)

Sources & evidence

ORD record
ord-ab8a4462af894e9f937cd471d7bb9fdf
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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