Hydrochloric Acid → 2-Ethyl-6-methylphenol
Reaction equation
Cl.N([O-])=O.[Na+].[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1N)[CH3:7].[OH:16]S(O)(=O)=O>O.CCO>[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1[OH:16])[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
19.4 mL (0.23 mmol) concentrated HCl and a solution of 16.1 g (0.23 mmol) sodium nitrite in water (approx. 70 mL) were added to a solution of 30 g (222 mmol) 2-ethyl-6-methyl-aniline in 135 mL EtOH at 0° C. and the mixture was stirred for 15 min. This mixture was added at 45° C. to a solution of 10.5 mL concentrated H2SO4 in 300 mL water and at the end of the addition heated to 70° C. The aqueous phase was cooled to RT and exhaustively extracted with EtOAc. The combined organic phases were extracted with 1 M NaOH solution. The aqueous phase was washed with DCM, acidified to pH 1 with 4 N HCl solution and extracted with DCM. The organic phase was washed with saturated NaCl solution, dried over Na2SO4 and evaporated down i.vac. The crude product was used in the next reaction step without any further purification.
Workup
- temperatureThe aqueous phase was cooled to RT
- extractionexhaustively extracted with EtOAc
- extractionThe combined organic phases were extracted with 1 M NaOH solution
- washThe aqueous phase was washed with DCM
- extractionextracted with DCM
- washThe organic phase was washed with saturated NaCl solution
- dry with materialdried over Na2SO4
- customevaporated down i.vac
- customThe crude product was used in the next reaction step without any further purification
Sources & evidence
- ORD record
- ord-2a428a71d8774525afa6044660cfdd87
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528129B2
Reaction notes
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