1.4- Dimethoxybenzene benzoyl chloride

Raja, T., Singh., A. R, Ramaswamy, A. V., Finiels, A. andMoreau, P. Benzoylation of 1,2-dimethoxybenzene with benzoic anhydride and substituted benzoyl chlorides over large pore zeolites, Appl. Catal., A, 2001, 211, 31-39. 

To 1,2-dimethoxybenzene (74.5 g) was added 3,4-dimethoxy-benzoyl chloride (98.2 grams) dissolved in 500ml CH2CI2, AICI3 (71.8 g) added, and the mixture stirred 3 hours at ambient temperature. Thereafter, the mixture was poured into 300 ml of a 1 1 mixture of ice and 1M HCl and stirred vigorously 15 minutes. The mixture was extracted twice with 100 ml CH2CI2 and washed with 50 ml of 10% NaOH followed by 50 ml water. The solvent was removed, a yellow solid isolated and re-crystallized in 95% ethyl alcohol, and 127 g product isolated, mp = 146-147 °C. 

Friedel-Crafts Acylation, Alkylation, and Related Reactions. While a stoichiometric amount of AICI3 is needed in Friedel-Crafts acylations, a small amount of Sc(OTf)3 smoothly catalyzes the same reaction. In the acetylation of thioanisole and o- or m-dimethoxybenzene, a single acetylated product is formed in an excellent yield. In the benzoylation of anisole, both benzoic anhydride and benzoyl chloride are effective, while benzoic anhydride gives a slightly higher yield. Addition of lithium perchlorate (LiC104) as a cocatalyst improves the yield dramatically (eq 13). ... 

Obtained by reaction of benzoyl chloride with 1,4-dimethoxybenzene in methylene chloride in the presence of stannic chloride at 0° (82%) [1503]. 

Acylation of anisole with A AN is carried out in a mixture of GALDEN SV 135, a suitable fluorous solvent, and chlorobenzene in the presence of hafnium tetra[bis(perfluorooctanesulfonyl)amide] (1% mol) at 70°C-120°C for 1 to 5 h, giving para-methoxyacetophenone in 80% yield and 100% selectivity. It is significant to underline that aluminum chloride gives the mentioned product in only 2% yield under the present mild reaction conditions. The catalyst can be very easily recycled by directly reusing the lower fluorous catalytic phase in the successive reaction with another mixture of reactants, affording the product more than three times without decrease in catalytic activity. The catalytic process can be applied to dimethoxybenzenes and mesitylene with both aliphatic and aromatic acyl chlorides and anhydrides (80%-97% yield). Benzoylation of toluene gives para-methylbenzophenone in 35% yield. 

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