Water → HCID 59164419, compound

HRID 906611Notes

Reaction equation

HRID 906611 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14].[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59164457HCID 59164457, compound

Product 1

HCID 59164419HCID 59164419, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-acetyl-2-nitro-benzoic acid methyl ester (1 g, 4.48 mmol) in MeOH (5 mL) was added NaBH4. The reaction mixture was stirred at r.t. for 24 h (TLC control). To the reaction mixture was added water until the appearance of a white turbid solution and the reaction was stirred for 15 min at r.t. MeOH was removed under reduced pressure. The aqueous phase was extracted with EtOAc three times. The combined organic phases were dried (Na2SO4) and concentrated in vacuo to afford 4-(1-hydroxy-ethyl)-2-nitro-benzoic acid methyl ester (0.742 g, 73%) as a brown oil which was used in the next step without further purification. rt 4.74 min.

Workup

  1. stirringthe reaction was stirred for 15 min at r.t
  2. customMeOH was removed under reduced pressure
  3. extractionThe aqueous phase was extracted with EtOAc three times
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bcca0eb0b484632a93a02bddbdf1532
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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