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

HRID 234920Notes

Reaction equation

HRID 234920 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-644d2beec96b458d835194edf2ea5d8a
Source dataset
uspto-grants-1997_01
Patent number
US05597827

Reaction notes

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