Methanol → 1,3-Di-tert-butylbenzene

HRID 2061948Notes

Reaction equation

HRID 2061948 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.[Na+].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 2723810Sodium FormateHCID 445427162,4-Di-tert-butylphenyl methanesulfonate

Product 1

HCID 1368101,3-Di-tert-butylbenzeneYield 98.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

In a nitrogen atmosphere, 2,4-di-tert-butylphenyl methanesulfonate (500 g, 1.76 mols), sodium formate (239 g, 3.52 mols), methanol (2400 g) and water (600 g) were mixed at 25° C., and with stirring, 10 mass % Pd/carbon (50 mass water-containing product) (30 g) (as metal palladium; 0.3 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. Still kept stirred, this was heated up to 65° C., taking 1 hour, and reacted for 6 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 (331 g, yield 99% by mass). The result is shown in Table I-1.

Workup

  1. stirringStill kept stirred
  2. customreacted for 6 hours
  3. customwas separated through filtration
  4. additionheptane (500 g) was added to the filtrate
  5. customThe organic layer obtained
  6. extractionafter extraction
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-5efca4c6f23d450e850202a9cc68f16c
Source dataset
uspto-grants-2012_10
Patent number
US08283508B2

Reaction notes

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