Sodium Bisulfate → HCID 23001252, compound

HRID 397843Notes

Reaction equation

HRID 397843 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:22])([F:21])[O:5][C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].S([O-])(O)(=O)=O.[Na+].[H][H]>C(Cl)Cl.C(O)(C)C.C(OCC)(=O)C.O>[F:3][C:4]([F:21])([F:22])[O:5][C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][OH:13]

Participants

9

Reactant 4

HCID 516919Sodium BisulfateHCID 4311764Sodium borohydrideHCID 23001216HCID 23001216, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23001252HCID 23001252, compoundYield 84.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (1.17 g, 31.2 mmol) was added to a solution of 2-(3-(trifluoromethoxy)phenoxy)benzaldehyde (6.28 g, 22.3 mmol) in a mixture of DCM (20 ml) and isopropanol (10 ml). The reaction mixture was stirred for 16 hours at room temperature. A 10% aqueous solution of sodium hydrogensulphate was added until the evolution of hydrogen had ceased. The mixture was diluted with ethyl acetate (200 ml). Water (200 ml) was added. The phases were separated. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (200 g), using ethyl acetate/heptane (1:2) as eluent, to give 5.34 g of [2-(3-(trifluoromethoxy)phenoxy)phenyl]methanol.

Workup

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (200 g)

Sources & evidence

ORD record
ord-5a0a562676ae476eb34b86f884f4a3ca
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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