4-chloro-2-ethylphenol

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

Procedure: 117.5 g (0.75 mol) 4-chloro-2-ethylphenol are dissolved with 42.25 g (0.25 mol) 4-isopropylbenzylchloride in 200 ml chloroform. 22.5 g water-free zinc chloride are added thereto for the alkylation reaction. Already at 30° C. a powerful reaction takes place. The entire mixture is after-stirred 5-6 h at 60° C. for completion of the alkylation. After a cooling it is subsequently washed three times each with 200 ml water, and then dried across sodium sulfate, after which the solvent chloroform is driven off. for the alkylation reaction Already at 30° C. a powerful reaction After a cooling it is subsequently washed three times each with 200 ml water dried across sodium sulfate

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

Procedure: 117.5 g (0.75 mol) 4-chloro-2-ethylphenol are dissolved with 42.25 g (0.25 mol) 4-isopropylbenzylchloride in 200 ml chloroform. 22.5 g water-free zinc chloride are added thereto for the alkylation reaction. Already at 30° C. a powerful reaction takes place. The entire mixture is after-stirred 5-6 h at 60° C. for completion of the alkylation. After a cooling it is subsequently washed three times each with 200 ml water, and then dried across sodium sulfate, after which the solvent chloroform is driven off. for the alkylation reaction Already at 30° C. a powerful reaction After a cooling it is subsequently washed three times each with 200 ml water dried across sodium sulfate

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

Procedure: To a solution of 4-chloro-2-ethyl-1-methoxybenzene (Preparation 5, 7.0 g, 41.0 mmol) in dichloromethane (20 mL) at 0° C. was added a 1M solution of boron tribromide in dichloromethane (20.5 mL, 20.5 mmol). After 2 hours, further boron tribromide solution (20 mL, 20.0 mmol) was added. After a further 2 hours, methanol was added and the reaction mixture concentrated in vacuo. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane) to afford the title compound (3.7 g, 58%). After a further 2 hours the reaction mixture concentrated in vacuo The residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane)

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

Procedure: To a stirred solution of 1.7 g (9.96 mmol) of 1-(5-chloro-2-hydroxyphenyl)ethanone in 20 mL of CH2Cl2 and 11.34 g (99.47 mmol) of trifluoroacetic acid, slowly add 3.46 g of (29.82 mmol) of triethylsilane. Stir resulting solution at room temperature for 18 hours, and remove volatiles and excess reagents under reduced pressure to give 1.52 g (97.4%) of 4-chloro-2-ethylphenol as an oil. 1H NMR (500 MHz, CDCl3) δ 7.09 (d, J=2.6 Hz, 1H), 7.03-7.01 (m, 1H), 6.65 (d, J=8.5 Hz, 1H), 4.82 (s, 1H), 2.58 (q, J=7.6 Hz, 2H) and 1.21 (t, J=7.6 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 151.85, 131.82, 129.62, 126.62, 125.60, 116.28, 22.81 and 13.60. MS m/e 157. The 4-chloro-2-ethylphenol can be used in Preparation 13b. resulting solution at room temperature for 18 hours remove volatiles and excess reagents under reduced pressure

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

Procedure: 117.5 g (0.75 mol) 4-chloro-2-ethylphenol are dissolved with 42.25 g (0.25 mol) 4-isopropylbenzylchloride in 200 ml chloroform. 22.5 g water-free zinc chloride are added thereto for the alkylation reaction. Already at 30° C. a powerful reaction takes place. The entire mixture is after-stirred 5-6 h at 60° C. for completion of the alkylation. After a cooling it is subsequently washed three times each with 200 ml water, and then dried across sodium sulfate, after which the solvent chloroform is driven off. for the alkylation reaction Already at 30° C. a powerful reaction After a cooling it is subsequently washed three times each with 200 ml water dried across sodium sulfate