Ammonium Chloride → 4-(3-Chloropropoxy)benzyl alcohol

HRID 657680Notes

Reaction equation

HRID 657680 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 35514794-(3-Chloropropoxy)-benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 228974964-(3-Chloropropoxy)benzyl alcoholYield 36.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-chloropropoxy)benzaldehyde (30 g) in methanol (250 mL), cooled at a temperature close to 0° C., is added portionwise sodium borohydride (7.72 g). The mixture is stirred for 4 hours, hydrolysed with a saturated aqueous solution of ammonium chloride and extracted with diethyl ether. The combined extracts are dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel (eluent: dichloromethane/methanol from 100/0 to 95/5). Fractions containing the expected product are pooled and concentrated under reduced pressure to give 11.1 g of 4-(3-chloropropoxy)benzyl alcohol as a white solid used without further purification.

Workup

  1. customclose to 0° C.
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined extracts are dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by chromatography over silica gel (eluent: dichloromethane/methanol from 100/0 to 95/5)
  6. additionFractions containing the expected product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f50778d797f44717a68091d26a3bc346
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

Loading…