1,4-Dihydro-2-methylbenzoic acid → 2-Methylbenzoic acid

HRID 2396554

Reaction equation

HRID 2396554 reaction equation
[CH3:1][C:2]1[CH:3]([CH:7]=[CH:8][CH2:9][CH:10]=1)[C:4]([OH:6])=[O:5].[Al]>C1C2C(CCCC2)CCC1.CCCCCC.[Rh]>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 3

HCID 5645811,4-Dihydro-2-methylbenzoic acidHCID 5359268AluminumHCID 178527255HCID 178527255, compound

Product 1

HCID 83732-Methylbenzoic acid

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 7044DecalinSolventHCID 8058HexaneSolvent

Procedure

To a suspension of 2-methyl-1,4-dihydrobenzoic acid (0.085g, 0.50 mmol; 81% pure, from Aldrich Chemical Company) in decalin (5 mL) under a nitrogen atmosphere is added a polysiloxane matrix material containing a homogenous dispersion of rhodium and aluminum (0.100 g). The solution is heated to reflux for 19 hours. On cooling the reaction mixture is diluted with hexane (25 mL) and extracted with aqueous sodium hydroxide (5%) solution (2×5 mL). The basic aqueous solution is acidified and extracted with chloroform (3×4 mL). The combined organic layer is dried over anhydrous sodium sulfate. The solvent is evaporated using a rotary evaporator to give 2-methylbenzoic acid.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 19 hours
  3. temperatureOn cooling the reaction mixture
  4. extractionextracted with aqueous sodium hydroxide (5%) solution (2×5 mL)
  5. extractionextracted with chloroform (3×4 mL)
  6. dry with materialThe combined organic layer is dried over anhydrous sodium sulfate
  7. customThe solvent is evaporated
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-039cbc08facb4bb6bef7f5c915d21b64
Source dataset
uspto-grants-1996_02
Patent number
US05492964

Linked notes

Loading…