Water → (2,6-Dimethyl-3-nitrophenyl)methanol

HRID 1106747Notes

Reaction equation

HRID 1106747 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([CH3:14])[C:3]=1[C:4](O)=[O:5].B.O>O1CCCC1>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([CH3:14])[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 2393292,6-Dimethyl-3-nitrobenzoic acid

Product 1

HCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanolYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
75 °C

Procedure

2,6-Dimethyl-3-nitrobenzoic acid (10 g) was dissolved in 100 ml of dry tetrahydrofuran and 165 ml of 1 M borane in tetrahydrofuran added. The mixture was heated to 75° C. for 4 hr. The mixture was cooled to room temperature and the excess reagent slowly decomposed with water and the solvent evaporated. The residue was treated with ethyl acetate, washed with 1M hydrochloric acid, then with water, dried, and evaporated to give 8.71 g of (2,6-dimethyl-3-nitro-phenyl)-methanol, mp 94.5-96.1° C. ##STR142##

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent evaporated
  3. additionThe residue was treated with ethyl acetate
  4. washwashed with 1M hydrochloric acid
  5. dry with materialwith water, dried
  6. customevaporated

Sources & evidence

ORD record
ord-5d9da7c398304be79c8f95d8ddea5aab
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

Loading…