37 6 37 5 37 4 37 3 32 8 32 7 31 1 29 2 28 9 28 0 24 8 24 5 22 8 22 7 21 1 20 6 19 8 19 7 13 0 12 1 11 8 ms esi m z 1272 m na dl u03b1 tocopherol succinate ii gt 150 g scale 2 5 7 8 tetramethyl 2 4 8 12 trimethyltridecyl chroman 6 ol dl u03b1 tocopherol 66 4 g 154 1 mmol and methylene chloride 300 ml were charged under nitrogen into a 1 l single necked round bottom flask which had been oven dried and cooled under vacuum succinic anhydride 23 1 g 231 mmol was added to the clear yellow solution followed by the addition of 4 dimethylaminopyridine 9 4 g 77 1 mmol and finally triethylamine 21 5 ml 154 mmol the reaction mixture was stirred at 23 u00b0 c overnight during which time the reaction mixture became a dark purplish solution hplc and tlc 3 7 etoac hexanes r f 0 3 indicated the reaction was complete the reaction mixture was poured into a 1 l separatory funnel and the flask rinsed with methylene chloride 300 ml the organic layer was washed with 1m hcl 160 ml u00d7 3 water 100 ml u00d7 2 and saturated aqueous sodium chloride solution 250 ml the organic layer was dried over sodium sulfate filtered and the solvent removed in vacuo affording a dark viscous oil the oil was poured onto a pad of silica gel 600 g in a 1 2 l filter funnel and then eluted first with methylene chloride 1.