Acetic Acid → (5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

HRID 2360516Notes

Reaction equation

HRID 2360516 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>ClCCl.CO.O>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH2:10][OH:11])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 584939905-Tert-butyl-2-methoxy-3-nitrobenzaldehyde

Product 1

HCID 58493934(5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3.47 g 5-tert-butyl-2-methoxy-3-nitro-benzaldehyde are dissolved in 15 ml dichloromethane and 15 ml of methanol, cooled to 0° C. and combined with 600 mg sodium borohydride. The mixture is allowed to come up to ambient temperature and stirred for 2 hours. Then the solvents are eliminated in vacuo, the residue is taken up in water and combined with 6 ml acetic acid. It is stirred vigorously for 5 minutes and then extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride solution, dried on magnesium sulphate and the solvents are eliminated in vacuo. The product thus obtained is further reacted directly.

Workup

  1. customto come up to ambient temperature
  2. stirringIt is stirred vigorously for 5 minutes
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. customdried on magnesium sulphate
  6. customThe product thus obtained
  7. customis further reacted directly

Sources & evidence

ORD record
ord-9c5028ee71e1488eb9826aef63929995
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

Loading…