Methanesulfonyl chloride → Methyl 4-(chloromethyl)benzoate

HRID 744175Notes

Reaction equation

HRID 744175 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.CS([Cl:17])(=O)=O>C(Cl)Cl>[Cl:17][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 36664Methyl 4-(chloromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 100 g (0.60175 moles) of methyl 4-hydroxymethylbenzoate in 600 mL of dry CH2Cl2. add 109 mL (79.1 g) of TEA and cool the so-formed reaction mixture to 0° C. Add, dropwise over a 2 hour period, 55.8 mL (0.722 mole, 1.2 eq) of methanesulfonyl chloride in 150 mL of dry CH2Cl2. Allow the so-formed stirred reaction mixture to warm slowly to room temperature over a 48 hr period. TLC shows no starting material remains. Add water, separate the layers and wash the organic layer successively with water, saturated NaHCO3 and brine. Dry the organic layer over Na2SO4. Remove the organic solvent under reduced pressure to produce 98.45 g of (88.6 % of theory) of the title compound as a crystalline solid. ##STR120##

Workup

  1. temperaturecool
  2. customthe so-formed reaction mixture to 0° C
  3. additionAdd, dropwise over a 2 hour period
  4. customreaction mixture
  5. customAdd water, separate the layers
  6. washwash the organic layer successively with water, saturated NaHCO3 and brine
  7. dry with materialDry the organic layer over Na2SO4
  8. customRemove the organic solvent under reduced pressure

Sources & evidence

ORD record
ord-caf55718d0604df68c11eaeb57219a8d
Source dataset
uspto-grants-1996_09
Patent number
US05559133

Reaction notes

Loading…