Hydrochloric Acid → 2-Ethyl-6-methylphenol

HRID 599787

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

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 at 0° C. to a solution of 30 g (222 mmol) 2-ethyl-6-methyl-aniline in 135 mL EtOH and stirred for 15 min. This mixture was added at 45° C. to a solution of 10.5 mL of 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 on Na2SO4 and concentrated by evaporation i.vac. The crude product was used in the subsequent 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
customdried on Na2SO4
concentrationconcentrated by evaporation i.vac
customThe crude product was used in the subsequent reaction step without any further purification

Sources & evidence

ORD record: ord-3cc2198c4e9746aca457ea706f961585
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897603B2

Linked notes

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