Methanesulfonic Acid → 2-Methyl-3-nitrobenzyl alcohol

HRID 1436853Notes

Reaction equation

HRID 1436853 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7].CS(O)(=O)=O>C1COCC1>[CH3:3][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 160962-Methyl-3-nitrobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 902892-Methyl-3-nitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

500 ml of THF and 76.5 gm NaBH4 was stirred for 30 min. at ambient temperature. Solution of 2-Methyl-3-nitro benzoic acid in THF (250 g in 750 ml) was added and stirred for 0.5 hour at ambient temperature. Further, methanesulphonic acid (90 ml) was added to the reaction mixture and stirred until the completion of reaction. The reaction mixture is extracted with ethyl acetate by addition of Hydrochloric acid and product organic layer is separated out. Ethyl acetate is evaporated to give 2-Methyl-3-nitrobenzyl alcohol as yellow oil, which is further treated with cyclohexane and crystallized to give 2-Methyl-3-nitrobenzyl alcohol (Yield: ˜210 g., 84%)

Workup

  1. stirringstirred until the completion of reaction
  2. extractionThe reaction mixture is extracted with ethyl acetate by addition of Hydrochloric acid and product organic layer
  3. customis separated out
  4. customEthyl acetate is evaporated

Sources & evidence

ORD record
ord-1d761842748b4b25815946e3b6b38806
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

Loading…