The Hoechst process for ibuprofen synthesis, developed by the Boots-Hoechst-Celanese company, was a significant improvement over...

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The Hoechst process for ibuprofen synthesis, developed by the Boots-Hoechst-Celanese company, was a significant improvement over the original Boots process. A synthetic scheme for this route follows. Though different reaction conditions are used, it begins like the Boots EKB1053(Chemical Engineering) SEPTEMBER 2018 5/5 CONFIDINTIAL process with a Friedel-Crafts acylation of isobutylbenzene to make 4'- isobutylacetophenone (4). This route differs dramatically in how this intermediate is transformed to ibuprofen, however. First, the aromatic ketone of (4) is reduced to an alcohol (9) via catalytic hydrogenation. Ibuprofen is produced directly from (9) through carbonylation with carbon monoxide in the presence of a palladium catalyst. Ac,0, HF H2(g), Pd/C OH Isobutylbenzene (2) (9) Co(g), PdCl,(PPh,)2 10% HCI(aq) он Ibuprofen (e) Outline the reactions when structure (9) reacts with the following (i) (ii) (iii) (iv) SOCI, Bra/H2O Benzoic acid Conc.H2SO4 (17°C) (4 marks) (f) List out any five reactions, which Ibuprofen can undergo to give desired product. (include reagents and conditions) (5 marks) The Hoechst process for ibuprofen synthesis, developed by the Boots-Hoechst-Celanese company, was a significant improvement over the original Boots process. A synthetic scheme for this route follows. Though different reaction conditions are used, it begins like the Boots EKB1053(Chemical Engineering) SEPTEMBER 2018 5/5 CONFIDINTIAL process with a Friedel-Crafts acylation of isobutylbenzene to make 4'- isobutylacetophenone (4). This route differs dramatically in how this intermediate is transformed to ibuprofen, however. First, the aromatic ketone of (4) is reduced to an alcohol (9) via catalytic hydrogenation. Ibuprofen is produced directly from (9) through carbonylation with carbon monoxide in the presence of a palladium catalyst. Ac,0, HF H2(g), Pd/C OH Isobutylbenzene (2) (9) Co(g), PdCl,(PPh,)2 10% HCI(aq) он Ibuprofen (e) Outline the reactions when structure (9) reacts with the following (i) (ii) (iii) (iv) SOCI, Bra/H2O Benzoic acid Conc.H2SO4 (17°C) (4 marks) (f) List out any five reactions, which Ibuprofen can undergo to give desired product. (include reagents and conditions) (5 marks)