9A18Z78Q73

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 3',4'-Diethyl-3,4-dimethoxybenzophenone was prepared analogously to 3,4-diethylbenzophenone using diethylbenzene (2.5 mL, 15 mmol), aluminum chloride (2.2 g, 16.5 mmol) and 3,4-dimethoxybenzoyl chloride (3 g, 15 mmol) with a reaction time of 3 hours at reflux. The crude product was purified by flash column chromatography (silica gel, 1.5% ethyl acetate/hexane) to afford 0.84 g (20%) of the product as an orange solid: mp 60-61° C.; 1H NMR (CDCl3) δ 7.74-7.15 (m, 5 H), 7.00-6.80 (m, 1 H) 3.96 (s, 3 H), 3.94 (s, 3 H), 2.93-2.60 (m, 4 H), 1.43-1.15 (m, 6 H); 13C NMR (CDCl3) δ 195.5, 152.7, 148.8, 146.3, 141.7, 135.9, 130.6, 129.8, 128.0, 127.7, 125.1, 112.2, 109.7, 56.0, 25.6, 25.4, 15.1, 15.0; Anal. Calcd for C19H22O3. Theoretical: C, 76.48; H, 7.43. Found: C, 76.53; H, 7.34. with a reaction time of 3 hours at reflux The crude product was purified by flash column chromatography (silica gel, 1.5% ethyl acetate/hexane)

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

Procedure: To a stirred ice bath cooled solution of diethylbenzene (1.7 mL, 10 mmol) in methylene chloride (30 mL) under nitrogen was added aluminum chloride (2.93 g, 22 mmol). A slight exotherm resulted. To the resulting reaction mixture was added benzoyl chloride (1.2 mL, 10 mmol). The reaction mixture was allowed to warm to room temperature and was then stirred at room temperature for 1.5 hours. The reaction mixture was poured into 60 mL of iced water and stirred for 20 minutes. The resulting mixture was extracted with methylene chloride (2×40 mL). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to afford the crude product as an orange oil. The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane) to afford 1.22 g (51%) of the product as a yellow oil: 1H NMR (CDCl3) δ 7.85-7.41 (m, 7 H), 7.30-7.20 (m, 1 H) 2.83-2.61 (m, 4 H), 1.35-1.17 (m, 6 H); 13C NMR (CDCl3) δ 196.8, 147.0, 141.9, 138.1, 135.3, 132.1, 132.1, 130.1,130.0, 128.1, 128.1, 25.6, 25.4, 15.1, 15.0; Anal. Calcd for C17H18O. Theoretical: C, 85.67; H, 7.61. Found: C, 85.38; H, 7.42. A slight exotherm resulted To the resulting reaction mixture stirred for 20 minutes The resulting mixture was extracted with methylene chloride (2×40 mL) The combined extracts were dried over magnesium sulfate concentrated in vacuo to afford the crude product as an orange oil The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-(3',4'-Diethylenzoyl) propanoic acid (m.p. 93° C, prepared by the acylation of 1,2-diethyl benzene with succinic anhydride) was catalytically reduced to 4-(3',4'-diethylphenyl) butanoic acid (b.p.0.7 143°-147° C). A mixture of this acid (59g; 0.27 mole) and 85% polyphosphoric acid (450g) was warmed to 80° C with stirring for 30 mins. and worked up as in example 8(a) to yield 48.30g (89%) of 6,7-diethyl-1-tetralone, b.p.0.7 118°-122° C. (Found; C, 82.95; H, 9.21; C14H18O requires; C, 83.12;H, 8.97%). Alternatively 4-(3', 4'-diethylphenyl )butanoic acid (23.3g; 0.106 mole) may be cyclised by stirring at 100° C with 80% sulphuric acid (115ml) for 11/2 hrs. After dilution, extraction into ether and distillation 15.53g (74%) of the tetralone was recovered.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: