Thionyl Chloride → (5-Methoxy-2-nitrophenyl)methanol

HRID 55835

Reaction equation

HRID 55835 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].O=S(Cl)Cl.[BH4-].[Na+]>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH2:8][OH:9])[CH:11]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 3392095-Methoxy-2-nitrobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 53405061(5-Methoxy-2-nitrophenyl)methanolYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

To a solution of 5-methoxy-2-nitrobenzoic acid (20.0 g, 0.102 mol) in anhydrous THF (200 mL) was added SOCl2 (20 mL), the mixture was refluxed for 4 hours. The solvent was removed under reduced pressure and the residue was dissolved in anhydrous THF (100 mL). The solution was added dropwise to a suspension of NaBH4 (7.70 g, 0.202 mol) in anhydrous THF (100 mL) and DMF (140 mL) at 0° C. over a period of 30 minutes. The mixture was stirred at 30° C. for 3 hours, then quenched with ice-water (100 mL) and basified by 2M NaOH to pH 8. An EtOAc workup was followed by removal of solvent in vacuo and purification by column chromatography (PE/EtOAc=1/1) to give the product (12.0 g, yield 66%).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in anhydrous THF (100 mL)
  4. customquenched with ice-water (100 mL)
  5. customAn EtOAc workup was followed by removal of solvent in vacuo and purification by column chromatography (PE/EtOAc=1/1)

Sources & evidence

ORD record
ord-83c9d71aedba45b680ed5d4dfa36553c
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Linked notes

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