2,4-Di-tert-butylphenol → HCID 86639499, compound

HRID 1037699Notes

Reaction equation

HRID 1037699 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.[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24]>C1(C)C=CC=CC=1.Cl>[CH2:23]([S:25]([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:27])=[O:26])[CH3:24]

Participants

6

Reactant 3

HCID 73112,4-Di-tert-butylphenol2×HCID 8471TriethylamineHCID 11667Ethanesulfonyl chloride

Product 1

HCID 86639499HCID 86639499, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

8.04 g (0.0389 mol) of 2,4-di-tert-butylphenol and 4.13 g (0.0408 mol) of triethylamine were dissolved in 15 mL of toluene followed by dropping in 5.01 g (0.0389 mol) of ethanesulfonyl 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 8.14 g (yield: 70%) of 2,4-di-tert-butylphenyl ethanesulfonate (white crystals, melting point: 76° C.).

Workup

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

Sources & evidence

ORD record
ord-844d2b3fb12a496ba7f77aef44116cd8
Source dataset
uspto-grants-2013_10
Patent number
US08546599B2

Reaction notes

Loading…