Carbon Dioxide → 4-Hydroxy-3,5-diisopropylbenzoic acid

HRID 1608486Notes

Reaction equation

HRID 1608486 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].C[O-].[Na+].[C:17](=[O:19])=[O:18]>CN(C)C(=O)C>[CH:10]([C:6]1[CH:7]=[C:8]([CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[OH:13])[C:17]([OH:19])=[O:18])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 4943PropofolHCID 10942334Sodium Methoxide

Product 1

HCID 259724-Hydroxy-3,5-diisopropylbenzoic acidYield 23%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

This acid was prepared according to the procedure of W. H. Meek et al. J. Chemical and Engineering Data, 14(3), 388, (1969). To a solution of 2,6-diisopropylphenol (Aldrich cat. #D12660-8) (37.0 ml, 0.20 mol) in anhydrous N,N-dimethylacetamide (150 ml) was added sodium methoxide (16.2 g, 0.30 mol). Carbon dioxide was passed through the mixture throughout the subsequent reaction period. The mixture was heated with stirring and the solvent was slowly distilled out during 2 hours of the period until the pot temperature reached to 180° C.. The mixture was allowed to continue stirring at 180° C. for another 1.5 hours and then cooled to 90° C. The flow of carbon dioxide was discontinued and water (400 ml) was added. The mixture, after further cooled to room temperature, was washed with toluene (4×60 ml) and then treated with conc. hydrochloric acid in an ice-water bath to pH 3. The resulting mixture was extracted with diethyl ether (2×150 ml); the ether extract was washed with brine (100 ml) and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave 3,5-diisopropyl-4-hydroxybenzoic acid (10.4 g, 23%). Rf 0.5 (silica gel, 50% diethyl ether/hexane). MS (CI, CH4): m/z 223 (M+1).

Workup

  1. customThis acid was prepared
  2. temperatureThe mixture was heated
  3. distillationthe solvent was slowly distilled out during 2 hours of the period until the pot temperature
  4. customreached to 180° C.
  5. stirringto continue stirring at 180° C. for another 1.5 hours
  6. additionwater (400 ml) was added
  7. temperatureThe mixture, after further cooled to room temperature
  8. washwas washed with toluene (4×60 ml)
  9. additiontreated with conc. hydrochloric acid in an ice-water bath to pH 3
  10. extractionThe resulting mixture was extracted with diethyl ether (2×150 ml)
  11. extractionthe ether extract
  12. washwas washed with brine (100 ml)
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a130e0e6b2604d75b0024ab1b1cbaa8d
Source dataset
uspto-grants-1995_03
Patent number
US05395752

Reaction notes

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