Ethyl Acetate → [2-(2,4-dichlorophenoxy)phenyl]methanol

HRID 397836Notes

Reaction equation

HRID 397836 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].S([O-])(O)(=O)=O.[Na+].C(OCC)(=O)C>C(O)(C)C.C(Cl)Cl>[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516919Sodium BisulfateHCID 27634272-(2,4-dichlorophenoxy)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2763668[2-(2,4-dichlorophenoxy)phenyl]methanolYield 72.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (119 mg, 3.15 mmol) was added to a solution of 2-(2,4-dichlorophenoxy)benzaldehyde (600 mg, 2.25 mmol) in isopropanol (10 ml) and DCM (20 ml). The reaction mixture was stirred for 2 hours at room temperature. A 10% aqueous solution of sodium hydrogensulphate (200 ml) was added dropwise. Ethyl acetate (300 ml) was added successively. The phases were separated. The aqueous phase was extracted with ethyl acetate (100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane 1:3 as eluent, to give 440 mg of 1-[2-(2,4-dichlorophenoxy)phenyl]methanol.

Workup

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (100 ml)
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml)
  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 (100 g)

Sources & evidence

ORD record
ord-cf8927e643d74c7bb859e972a021e2c0
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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