Acetyl chloride → 1-(2-Hydroxy-3-methyl-4-nitro-phenyl)-ethanone
Reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[Al+3].[Cl-].[Cl-].[Cl-].[C:16](Cl)(=[O:18])[CH3:17]>[N+](C1C=CC=CC=1)([O-])=O>[OH:11][C:3]1[C:2]([CH3:1])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:5][C:4]=1[C:16](=[O:18])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-methyl-3-nitrophenol (2.0 g, 13 mmol) in nitrobenzene (16 mL) at RT under Ar gas is added AlCl3 (3.9 g, 29 mmol). The reddish mixture is heated to 50° C. To the reddish mixture is added dropwise via addition funnel a solution of acetyl chloride (1.2 mL, 17 mmol) in nitrobenzene (10 mL). The reaction is heated to 120° C. After 2 h at 120° C., the reaction mixture is cooled to RT and quenched slowly into a 1N HCl/ice mixture. The resulting mixture is stirred for 30 min and extracted with EtOAc (3×). The organic layers are combined and concentrated. Water is used to azeotrope off the nitrobenzene. The resulting residue is purified by flash column chromatography using 20% EtOAc/hexane. Obtained is the title compound as reddish oil (1.2 g). The title compound is 60% pure by LC-MS. Compound is used as is in the next step. LC-MS (m/e): 194 (M−1).
Workup
- temperatureThe reaction is heated to 120° C
- temperaturethe reaction mixture is cooled to RT
- customquenched slowly into a 1N HCl/ice mixture
- extractionextracted with EtOAc (3×)
- concentrationconcentrated
- customThe resulting residue is purified by flash column chromatography
- customObtained
Sources & evidence
- ORD record
- ord-1e2016d93f77403aac8e1fdadfe78e4e
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816523B2
Reaction notes
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