Ethyl Acetate → (2-Chloro-5-methoxy-4-nitrophenyl)methanol

HRID 1019769Notes

Reaction equation

HRID 1019769 reaction equation
[Li+].[BH4-].[Cl:3][C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[CH:10][C:5]=1[C:6](OC)=[O:7].CCOC(C)=O.[NH4+].[Cl-]>C1COCC1>[Cl:3][C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[CH:10][C:5]=1[CH2:6][OH:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 67465993Methyl 2-chloro-5-methoxy-4-nitrobenzoate

Product 1

HCID 67465960(2-Chloro-5-methoxy-4-nitrophenyl)methanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2M solution of LiBH4 in THF (2 mmol) was added drop-wise to a stirred solution of methyl 2-chloro-5-methoxy-4-nitrobenzoate (1 mmol) in dry THF (10 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 5 hours. EtOAc (10 mL) was added to the mixture followed by saturated NH4Cl solution (2 mL) and stirring continued for 15 minutes. The mixture was partitioned between EtOAc (10 mL) and water (10 mL) and the separated aqueous phase was extracted with EtOAc (10 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (89%) which was used without further purification.

Workup

  1. stirringstirring
  2. waitcontinued for 15 minutes
  3. customThe mixture was partitioned between EtOAc (10 mL) and water (10 mL)
  4. extractionthe separated aqueous phase was extracted with EtOAc (10 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b68e6076d8c4cd4ad11b38911350218
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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