4-Toluenesulfonyl chloride → 3-Methoxypropyl 4-methylbenzenesulfonate

Participants

Reaction Steps

37.9 g of 3-methoxypropanol and 53.9 g of p-toluenesulfonyl chloride in 50.2 g of pyridine were stirred for 3 hours while the reaction temperature is kept at 0 to 10° C. The product was extracted with ethyl acetate, to give 91.2 g of 3-methoxypropyl tosylate (yield: 89%). 55 g of the obtained 3-methoxypropyl tosylate and 39.0 g of 2,3,3,5-tetramethyl-3H-indole were blended at 120° C. for 3 hours and was cooled to room temperature. 47.7 g of 2,5-bis[(phenylamino)methylene]cyclopentylidenediphenylaminium tetrafluoroborate, 23.0 g of acetic anhydride, 56.9 g of triethylamine, and 220 ml of 2-propanol were added thereto, and the mixture was further stirred at 80° C. for 3 hours. After reaction, the mixture was allowed to cool to room temperature, and 90 ml of water was added thereto. The crystal precipitated was collected by filteration, and was washed sufficiently with water, to give 60.1 g of a cyanine colorant (IR-2) (yield: 80%). 15.0 g of the colorant (IR-2) obtained was dissolved in 90 ml of acetonitrile. The mixture was added dropwise into an aqueous solution containing 6.6 g of KPF6 in 90 g of water at room temperature over 15 minutes, and the resulting mixture was stirred for 2 hours after the dropwise addition. Then, the crystal precipitated was collected by filteration and dried, to give 15.2 g of a cyanine colorant (IR-3) (yield: 95%). Then, 5.0 g of the cyanine colorant obtained (IR-3) was dissolved in 50 ml of chloroform, 3.0 g of manganese dioxide was added thereto, and the mixture was stirred at room temperature for 48 hours. After removal of manganese dioxide by filtration, the filtrate was distilled for removal of chloroform, and the crude crystal obtained was resuspended in 20 ml of ethyl acetate, to give 4.5 g of (A-4) (yield: 90%).

Provenance & Evidence