Triethylamine → 3,5-Di-tert-butylphenyl ethanesulfonate

HRID 1037703

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24]>C1(C)C=CC=CC=1>[CH2:23]([S:25]([O:15][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1)(=[O:27])=[O:26])[CH3:24]

Participants

Conditions

Temperature: 25 °C

Procedure

2.50 g (0.012 mol) of 3,5-di-tert-butylphenol and 1.27 g (0.013 mol) of triethylamine were dissolved in 15 mL of toluene followed by dropping in 1.62 g (0.013 mol) of ethanesulfonyl chloride over the course of 10 minutes at 5° C. Following completion of dropping, the mixture was stirred for 2 hours at 25° C. and the 3,5-di-tert-butylphenol was confirmed to no longer be present. The reaction liquid was placed in ice water and following separation of the organic layer, was washed twice with saturated brine followed by drying with MgSO4 and concentrating to obtain 3.27 g (yield: 91%) of 3,5-di-tert-butylphenyl ethanesulfonate. A purified product crystallized with n-hexane (white crystals, melting point: 52° C.) was used in a battery test.

Workup

customThe reaction liquid
customseparation of the organic layer
washwas washed twice with saturated brine
dry with materialby drying with MgSO4
concentrationconcentrating

Sources & evidence

ORD record: ord-fe98c886bdab41f09ffa4b4644d7af53
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546599B2

Linked notes

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