3-Chloro-4-methyl-5-nitrobenzoic acid → (3-Chloro-4-methyl-5-nitrophenyl)methanol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[CH3:11])[C:5](O)=[O:6]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[CH3:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4.2 g of 3-chloro-4-methyl-5-nitro benzoic acid was dissolved in 20 ml dry THF and the solution was cooled to 0° C. BH3 -THF (28 ml) solution was added in 2 ml portions. After 1 hr, the reaction mixture was poured onto 100 g of ice containing saturated NaHCO3 solution. The mixture was extracted with ether (3×75 ml). The extracts were washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. The resultant brown oil was applied to a SiO2 column as a solution in toluene and eluted with 25% ethyl acetate in hexane to give 1.96 g of (3-chloro-4-methyl-5-nitrophenyl)methanol.
Workup
- extractionThe mixture was extracted with ether (3×75 ml)
- washThe extracts were washed with brine
- dry with materialdried (anhydrous MgSO4)
- filtrationfiltered
- concentrationconcentrated
- washeluted with 25% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-99401c4c6d1f4eb9a08b8f5eafe278c8
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06057349
Reaction notes
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