2-(Carboxymethyl)-4-nitrobenzoic acid → 2-(2-(Hydroxymethyl)-5-nitrophenyl)ethanol

HRID 580938Notes

Reaction equation

HRID 580938 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2]>C1COCC1>[OH:8][CH2:7][C:6]1[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:5]=1[CH2:4][CH2:1][OH:2]

Participants

3

Reactant 1

HCID 71720252-(Carboxymethyl)-4-nitrobenzoic acid

Product 1

HCID 107265862-(2-(Hydroxymethyl)-5-nitrophenyl)ethanolYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF (60 mL) solution of 2-carboxymethyl-4-nitro-benzoic acid (3.0 g , 13.3 mmol) was treated with borane-THF complex (53.3 mL, 53.3 mmol) over 15 min at 0° C. The reaction was stirred for 18.5 hrs, quenched with THF/water (1:1, 30 mL), water (20 mL) added and the layers separated. The aqueous layer was reextracted with THF (30 mL); the combined organic phase washed with brine, dried with magnesium sulfate, and solvent removed under vacuum to give the product as a white solid (2.06 g, 78%) mp=79-81° C.

Workup

  1. customquenched with THF/water (1:1, 30 mL), water (20 mL)
  2. additionadded
  3. customthe layers separated
  4. washthe combined organic phase washed with brine
  5. dry with materialdried with magnesium sulfate, and solvent
  6. customremoved under vacuum

Sources & evidence

ORD record
ord-aea0da7d72a74c94bfa40cbd484c7c0d
Source dataset
uspto-grants-1999_07
Patent number
US05919795

Reaction notes

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