Sodium borohydride → 2-n-Pentyl-3-(2,4-dichlorophenyl)-allyl alcohol

HRID 2418266Notes

Reaction equation

HRID 2418266 reaction equation
[BH4-].[Na+].[CH2:3]([C:8](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH:9]=[O:10])[CH2:4][CH2:5][CH2:6][CH3:7]>CO>[CH2:3]([C:8](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:9][OH:10])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 538223112-n-Pentyl-3-(2,4-dichlorophenyl)-acrolein

Product 1

HCID 540602872-n-Pentyl-3-(2,4-dichlorophenyl)-allyl alcoholYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

54.5 g of NaBH4 were added, in portions, to a solution of 150 g of (I) in 1.5 l of methanol. The mixture was refluxed for 1 hour and then concentrated, 1 l of 2N HCl was added, and the mixture was refluxed for a further hour and then extracted with CH2Cl2. The organic phase was washed with water, dried over Na2SO4 and concentrated. Distillation of the residue gave 93 g of (II) of boiling point 156°-160° C./0.2 mbar.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated
  3. addition1 l of 2N HCl was added
  4. temperaturethe mixture was refluxed for a further hour
  5. extractionextracted with CH2Cl2
  6. washThe organic phase was washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-f00997a6b580433c94373ce5b12f620f
Source dataset
uspto-grants-1984_09
Patent number
US04472412

Reaction notes

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