Water → HCID 86639501, compound

HRID 1037700Notes

Reaction equation

HRID 1037700 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>CCOCC.C1(C)C=CC=CC=1>[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([O:17][C:8]2[CH:9]=[CH:10][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:12][C:7]=2[C:3]([CH3:6])([CH3:5])[CH3:4])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73112,4-Di-tert-butylphenol2×HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydride

Product 1

HCID 86639501HCID 86639501, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

1.02 g (0.026 mol) of 60% oil-dispersed sodium hydride were dissolved in 20 mL of ether and cooled to 5° C. 20 mL of an ether solution containing 5.00 g (0.024 mol) of 2,4-di-tert-butylphenol were dropped in over the course of 15 minutes at 5° C. and stirred for 30 minutes followed by dropping in 20 mL of a toluene solution containing 4.16 g (0.022 mol) of p-toluenesulfonyl chloride over the course of 20 minutes, stirring for 30 minutes at 25° C. and confirming the 2,4-di-tert-butylphenol to no longer be present. Following completion of the reaction, water was added and the organic layer was extracted with ethyl acetate followed by washing twice with saturated aqueous NaHCO3 solution and once with saturated brine, drying with MgSO4 and concentrating. The resulting crystals were purified by crystallizing with n-hexane to obtain 3.0 g (yield: 38%) of 2,4-di-tert-butylphenyl p-toluenesulfonate (white crystals, melting point: 81° C.).

Workup

  1. additionwere dropped in over the course of 15 minutes at 5° C.
  2. stirringstirring for 30 minutes at 25° C.
  3. additionwas added
  4. extractionthe organic layer was extracted with ethyl acetate
  5. washby washing twice with saturated aqueous NaHCO3 solution and once with saturated brine
  6. dry with materialdrying with MgSO4
  7. concentrationconcentrating
  8. customThe resulting crystals were purified
  9. customby crystallizing with n-hexane

Sources & evidence

ORD record
ord-391f24baaaa74523adeb23cea80d9cc8
Source dataset
uspto-grants-2013_10
Patent number
US08546599B2

Reaction notes

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