2,3,5-Trichlorobenzaldehyde → Benzene, 1,2,5-trichloro-3-methoxy-

HRID 846354Notes

Reaction equation

HRID 846354 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 925962,3,5-TrichlorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 41018Benzene, 1,2,5-trichloro-3-methoxy-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,3,5-trichlorobenzaldehyde (Aldrich, 50 gms) in ethanol (1.0 L) at room temperature was added NaBH4 (7.00 gms) and the resulting mixture stirred for 3.5 hours. The reaction was quenched with water, and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid. 43.00 gms, mp. 90°-93° C.

Workup

  1. customThe reaction was quenched with water
  2. customthe solvent evaporated in vacuo
  3. custombefore partitioning the residue between CHCl3 and saturated NaHCO3 solution
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto leave a white solid

Sources & evidence

ORD record
ord-1189aece217648e188fd6941c40d09de
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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