5-Methoxy-2-nitrobenzoic acid → (5-Methoxy-2-nitrophenyl)methanol

HRID 525420Notes

Reaction equation

HRID 525420 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]>C1COCC1.O>[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

4

Reactant 1

HCID 3392095-Methoxy-2-nitrobenzoic acid

Product 1

HCID 53405061(5-Methoxy-2-nitrophenyl)methanolYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 5-methoxy-2-nitrobenzoic acid (20 g, 1.0 mol) in THF (100 mL) was added BH3 (1.0 M in THF, 30.4 mL, 3.0 eq) at 0° C. The mixture was refluxed for 3 h, diluted with water (200 mL) and extracted with DCM (100 ml*3). The combined organic lays were dried over MgSO4, evaporated to afford (5-methoxy-2-nitrophenyl)methanol (18 g, yield: 97%), as a white solid. 1HNMR (400 MHz, DMSO-d6) δ: 8.13 (d, J=6.4 Hz, 1H), 7.34 (d, J=6.4 Hz, 1H), 7.02 (s, 1H), 5.60˜5.58 (m, 1H), 4.84 (d, J=8.0 Hz, 2H), 3.89 (s, 3H); ESI-MS: m/z 184.1 ([M+1]+).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. extractionextracted with DCM (100 ml*3)
  3. dry with materialThe combined organic lays were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-9909f15f78934464b09829d0b1dba954
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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