2,4-Di-tert-butylphenol → 2,4-Di-tert-butylphenyl methanesulfonate

HRID 1037698Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C1(C)C=CC=CC=1.Cl>[CH3:23][S:24]([O:15][C:6]1[CH:7]=[CH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:26])=[O:25]

Participants

Conditions

Temperature: 25 °C

Procedure

21.00 g (0.102 mol) of 2,4-di-tert-butylphenol and 11.84 g (0.117 mol) of triethylamine were dissolved in 200 mL of toluene followed by dropping in 12.24 g (0.107 mol) of methanesulfonyl chloride over the course of 30 minutes at 10° C. Following completion of dropping, the mixture was stirred for 2 hours at 25° C. and the 2,4-di-tert-butylphenol was confirmed to no longer be present. The reaction liquid was placed in 3% aqueous hydrochloric acid solution and following separation of the organic layer, was washed once with saturated aqueous NaHCO3 solution and twice with saturated brine followed by drying with MgSO4 and concentrating. The resulting crude crystals were purified by crystallization with n-heptane to obtain 25.8 g (yield: 90%) of 2,4-di-tert-butylphenyl methanesulfonate (white crystals, melting point: 63° C.).

Workup

customThe reaction liquid
customseparation of the organic layer
washwas washed once with saturated aqueous NaHCO3 solution and twice with saturated brine
dry with materialby drying with MgSO4
concentrationconcentrating
customThe resulting crude crystals were purified by crystallization with n-heptane

Sources & evidence

ORD record: ord-e5df211c89ad46a4a4232bdf09759a43
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546599B2

Reaction notes

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