Sodium borohydride → {4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

HRID 2194861Notes

Reaction equation

HRID 2194861 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[BH4-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 579560774-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]benzaldehyde

Product 1

HCID 67447508{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the aldehyde from Step 2 (1 eq.) in a mixture of THF/MeOH (2/1, 0.21M) was added portion wise sodium borohydride (1.5 eq.). The mixture was stiffed 3 h at room temperature, quenched slowly with 1N HCl and finally concentrated in vacuo. The residual aqueous phase was extracted with diethylether twice. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Stirring the residue in 10% Et2O/Hex for 4 h followed by filtration afforded the desired alcohol as a white crystalline solid.

Workup

  1. customquenched slowly with 1N HCl
  2. concentrationfinally concentrated in vacuo
  3. extractionThe residual aqueous phase was extracted with diethylether twice
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-062e222120974d5cb3fbde44196a10f5
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

Loading…