2,6-Dichloro-4-hydroxybenzaldehyde → (4-Benzyloxy-2,6-dichloro-phenyl)methanol

HRID 2235235Notes

Reaction equation

HRID 2235235 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CCO>[CH2:4]([O:10][C:8]1[CH:9]=[C:2]([Cl:1])[C:3]([CH2:4][OH:5])=[C:6]([Cl:11])[CH:7]=1)[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=1

Participants

4

Reactant 2

HCID 5283822,6-Dichloro-4-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 66621751(4-Benzyloxy-2,6-dichloro-phenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Suspend 2,6-dichloro-4-hydroxy-benzaldehyde in 3 L EtOH and cool in an ice bath at 0° C. Add 32.97 g (871.45 mmol) NaBH4 caplets portionwise. Remove the ice bath and stir for 2 hours. Carefully add the reaction mixture to 8 L sat'd. NH4Cl solution and stir until fully quenched. Extract with CH2Cl2 (2×2 L) and dry the combined organic extracts over Na2SO4. Filter and concentrate under vacuum to yield 247 g (100%) of (4-benzyloxy-2,6-dichloro-phenyl)methanol as a white solid.

Workup

  1. customRemove the ice bath
  2. additionCarefully add the reaction mixture to 8 L
  3. stirringNH4Cl solution and stir
  4. customuntil fully quenched
  5. extractionExtract with CH2Cl2 (2×2 L)
  6. dry with materialdry the combined organic extracts over Na2SO4
  7. filtrationFilter
  8. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-56b2d48822634ad48d24517f966f3bf6
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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