Formic Acid → 1,3-Di-tert-butylbenzene

HRID 2061953Notes

Reaction equation

HRID 2061953 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.[Cl-].[Li+].CO>[Pd].[C].[Pd].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

8

Reactant 4

HCID 284Formic AcidHCID 887MethanolHCID 433294Lithium ChlorideHCID 445427162,4-Di-tert-butylphenyl methanesulfonate2×

Product 1

HCID 1368101,3-Di-tert-butylbenzeneYield 76.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418390HCID 178418390, compoundCatalyst2×HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere under normal pressure, 2,4-di-tert-butylphenyl methanesulfonate (30 g, 0.11 mols), formic acid (9.7 g, 0.21 mols), lithium chloride (8.9 g, 0.21 mols) and methanol (180 g) were mixed at 25° C., and with stirring, 10 mass % Pd/carbon (50 mass % water-containing product) (6 g) as supported by a carbon carrier having a specific surface area of 780 m2/g (by BET method) (as metal palladium; 1 mass relative to 2,4-di-tert-butylphenyl methanesulfonate) was put into it. With stirring, the reaction liquid was reacted at the same temperature for 9 hours. Water (10 mL) was added to the reaction liquid and Pd-carbon was separated through filtration, then heptane (30 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 (16 g, yield 81% by mass). The result is shown in Table II-2.

Workup

  1. stirringWith stirring
  2. customthe reaction liquid
  3. customwas reacted at the same temperature for 9 hours
  4. customwas separated through filtration
  5. additionheptane (30 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-2211cd3274214578ba41573f56537031
Source dataset
uspto-grants-2012_10
Patent number
US08283508B2

Reaction notes

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