Hydrochloric Acid → 4-(3,4-Dichlorophenyl)-5-hydroxypent-1-ene

HRID 1533042Notes

Reaction equation

HRID 1533042 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH:15]=[O:16])[CH2:12][CH:13]=[CH2:14])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl>C(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:15][OH:16])[CH2:12][CH:13]=[CH2:14])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 106094362-(3,4-Dichlorophenyl)pent-4-enal

Product 1

HCID 225936544-(3,4-Dichlorophenyl)-5-hydroxypent-1-eneYield 53.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (2.2 g) was added in four portions, over 10 minutes, to an ice-cooled solution of 4-(3,4-dichlorophenyl)-4-formylbut-1-ene (13 g) (see Preparation 21) in ethanol (100 ml). The mixture was stirred for a further 30 minutes before removing the solvent under reduced pressure to give a residue. This was suspended in water (50 ml), cooled to 0° C. and the mixture acidified (pH<6) with 2N aqueous hydrochloric acid solution. The mixture was extracted three times with dichloromethane, the organic phases combined and the solvent removed under reduced pressure. Dichloromethane (200 ml) was then added, the mixture stirred and filtered and the solvent removed from the filtrate under reduced pressure to give an oil. This was chromatographed on silica gel eluting with dichloromethane to give 4-(3,4-dichlorophenyl)-5-hydroxypent-1-ene (7 g) as a orange oil.

Workup

  1. custombefore removing the solvent under reduced pressure
  2. customto give a residue
  3. extractionThe mixture was extracted three times with dichloromethane
  4. customthe solvent removed under reduced pressure
  5. additionDichloromethane (200 ml) was then added
  6. stirringthe mixture stirred
  7. filtrationfiltered
  8. customthe solvent removed from the filtrate under reduced pressure
  9. customto give an oil
  10. customThis was chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-c296aac1f15e4035adb11d413e3743d4
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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