Triethylamine → 3-Tert-butylphenyl methanesulfonate

HRID 1037704Notes

Reaction equation

HRID 1037704 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C1(C)C=CC=CC=1.O>[CH3:19][S:20]([O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11450Phenol, 3-(1,1-dimethylethyl)-2×HCID 31297Methanesulfonyl chloride

Product 1

HCID 594641483-Tert-butylphenyl methanesulfonateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

8.00 g (53.3 mol) of 3-tert-butylphenol and 5.93 g (58.6 mol) of triethylamine were dissolved in 80 mL of toluene followed by dropping in 6.71 g (58.6 mol) of methanesulfonyl chloride over the course of 10 minutes at 10° C. followed by stirring for 10 minutes at 25° C. and confirming the 3-tert-butylphenol to no longer be present by gas chromatography. The reaction liquid was placed in water and following separation of the organic layer, was washed three times with water, once with saturated aqueous NaHCO3 solution and once with saturated brine followed by drying with MgSO4, concentrating and purifying the resulting residue by vacuum distillation to obtain 10.7 g (yield: 88%) of 3-tert-butylphenyl methanesulfonate.

Workup

  1. customThe reaction liquid
  2. customseparation of the organic layer
  3. washwas washed three times with water
  4. dry with materialby drying with MgSO4
  5. concentrationconcentrating
  6. custompurifying the resulting residue
  7. distillationby vacuum distillation

Sources & evidence

ORD record
ord-4fe6647686ae495087c803913e58b2fd
Source dataset
uspto-grants-2013_10
Patent number
US08546599B2

Reaction notes

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