4-chloro-2,3-dimethylphenol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 4-chloro-3-methylcresol (15.0 g; 0.105 mol), N,N-diisopropylethylamine (23.3 ml; 0.137 mol) and THF (150 ml), was added dropwise chloromethylmethyl ether (9.50 ml; 0.126 mol) at room temperature. The mixture was stirred at 60° C. for 27.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1) to give 2-chloro-5-(methoxyethoxy)toluene as dark reddish-brown oil (17.7 g; 90%). extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous sodium sulphate evaporated under reduced pressure The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 4-chloro-3-methylcresol (15.0 g; 0.105 mol), N,N-diisopropylethylamine (23.3 ml; 0.137 mol) and THF (150 ml), was added dropwise chloromethylmethyl ether (9.50 ml; 0.126 mol) at room temperature. The mixture was stirred at 60° C. for 27.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1) to give 2-chloro-5-(methoxyethoxy)toluene as dark reddish-brown oil (17.7 g; 90%). extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous sodium sulphate evaporated under reduced pressure The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 4-chloro-3-methylcresol (15.0 g; 0.105 mol), N,N-diisopropylethylamine (23.3 ml; 0.137 mol) and THF (150 ml), was added dropwise chloromethylmethyl ether (9.50 ml; 0.126 mol) at room temperature. The mixture was stirred at 60° C. for 27.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1) to give 2-chloro-5-(methoxyethoxy)toluene as dark reddish-brown oil (17.7 g; 90%). extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous sodium sulphate evaporated under reduced pressure The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=5:1)