Methanol → 1,3-Di-tert-butylbenzene

HRID 2061950Notes

Reaction equation

HRID 2061950 reaction equation
CS(O[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O.C([O-])=O.[Li+].CO>[Pd].[C].O>[C:12]([C:9]1[CH:10]=[CH:11][CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 23680280Lithium formateHCID 445427162,4-Di-tert-butylphenyl methanesulfonate

Product 1

HCID 1368101,3-Di-tert-butylbenzeneYield 99.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere under normal pressure, 2,4-di-tert-butylphenyl methanesulfonate (500 g, 1.76 mols), lithium formate (183 g, 3.52 mols) and methanol (3000 g) were mixed at 25° C., and with stirring, 10 mass % Pd/carbon (50 mass % water-containing product) (100 g) (as metal palladium; 1 mass % relative to 2,4-di-tert-butylphenyl methanesulfonate) as supported by a carbon carrier having a specific surface area of 780 m2/g (by BET method) was put into it. With stirring, the reaction liquid was reacted at the same temperature for 4 hours. Water (100 mL) was added to the reaction liquid and Pd-carbon was separated through filtration, then heptane (500 g) was added to the filtrate. The organic layer obtained after extraction was concentrated under reduced pressure to give crude 1,3-di-tert-butylbenzene (334 g, yield 100% by mass).

Workup

  1. stirringWith stirring
  2. customthe reaction liquid
  3. customwas reacted at the same temperature for 4 hours
  4. customwas separated through filtration
  5. additionheptane (500 g) was added to the filtrate
  6. customThe organic layer obtained
  7. extractionafter extraction
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-016669ea2bd44e0b8a3f68feac687b37
Source dataset
uspto-grants-2012_10
Patent number
US08283508B2

Reaction notes

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