Hydrochloric Acid → Pentanol, 4-methyl-4-nitro-

HRID 1744017Notes

Reaction equation

HRID 1744017 reaction equation
[CH3:1][C:2]([N+:10]([O-:12])=[O:11])([CH3:9])[CH2:3][CH2:4][C:5](OC)=[O:6].[BH4-].[Na+].O.Cl>C(O)C>[CH3:1][C:2]([N+:10]([O-:12])=[O:11])([CH3:9])[CH2:3][CH2:4][CH2:5][OH:6]

Participants

6

Conditions

Temperature
5 °C

Procedure

Methyl 4-methyl-4-nitropentanoate (17.5 g, 0.1 mol) was dissolved in ethanol (200 ml) and cooled to 5° C., after which sodium borohydride (7.55 g, 0.2 mol) was added. The mixture was stirred at room temperature for 1 h, and at 50° C. for 3 h. Water (100 ml) and hydrochloric acid were added to adjust the pH to 3, and ethanol was evaporated by concentration under reduced pressure. The residue was extracted with ethyl acetate (250 ml) and water (100 ml) and washed with saturated brine. Ethyl acetate was evaporated by concentration under reduced pressure to give the objective compound (14.7 g, yield 91.2%).

Workup

  1. waitat 50° C. for 3 h
  2. customwas evaporated by concentration under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (250 ml) and water (100 ml)
  4. washwashed with saturated brine
  5. customEthyl acetate was evaporated by concentration under reduced pressure

Sources & evidence

ORD record
ord-d63b88b4506b4ef68622ca524d0d8d27
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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