Methanol → (5-Methyl-2-nitrophenyl)methanol

HRID 1758231Notes

Reaction equation

HRID 1758231 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].CO>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 183715-Methyl-2-nitrobenzoic acid

Product 1

HCID 568847(5-Methyl-2-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 ml of borane-dimethyl sulphide complex are added over the course of 30 minutes to a boiling solution of 100 g of 5-methyl-2-nitrobenzoic acid in 750 ml of tetrahydrofuran. The reaction solution is boiled for 4 hours under reflux conditions. Then, 200 ml of methanol are added with cooling, and the solution is left to stand for 30 minutes at room temperature. It is then evaporated in a vacuum until dry and the residue thus obtained is partitioned between chloroform and sodium carbonate solution. The organic phase is washed with water, dried over sodium sulphate and evaporated, whereupon the heading compound is obtained as a crystalline solid having a low melting point.

Workup

  1. temperaturewith cooling
  2. waitthe solution is left
  3. waitto stand for 30 minutes at room temperature
  4. customIt is then evaporated in a vacuum
  5. customuntil dry
  6. customthe residue thus obtained
  7. customis partitioned between chloroform and sodium carbonate solution
  8. washThe organic phase is washed with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated, whereupon the heading compound
  11. customis obtained as a crystalline solid

Sources & evidence

ORD record
ord-9a33651ec22d48e68368da9797132fcf
Source dataset
uspto-grants-1983_02
Patent number
US04372956

Reaction notes

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