Citric Acid → (2-Isopropoxyphenyl)methanol

HRID 384115Notes

Reaction equation

HRID 384115 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl.[BH4-].[Na+].[C:19](O)(=O)[CH2:20][C:21](CC(O)=O)(C(O)=O)O>CN(C)C=O.BrC(C)C.CO>[CH:20]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH3:21])[CH3:19]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 4311764Sodium borohydride

Product 1

HCID 12071269(2-Isopropoxyphenyl)methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 63582-BromopropaneSolvent

Procedure

To a solution of 2-hydroxybenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 1.35 ml of 2-bromopropane and 1.98 g of potassium carbonate were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in methanol (5 ml), 362 mg of sodium borohydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customto afford a crude product as a yellow oil
  6. temperaturecooling
  7. stirringthe reaction solution was stirred at room temperature for 30 minutes
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe combined organic layers were washed with a saturated saline solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue obtained
  13. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))

Sources & evidence

ORD record
ord-6bf5fc07978646e39906b94f6909d3bd
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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