4-Toluenesulfonyl chloride → 1,5-Pentanediol monotosylate

To a solution of 1,5-pentanediol (30 g, 0.29 mol) in dichloromethane/DMF (15/1, 320 ml) were added triethylamine (38.1 ml, 0.274 mol), dimethylaminopyridine (7.04 g, 57.6 mmol) and p-toluenesulfonic acid chloride (49.42 g, 0.259 mol) were in turn added at -30° C. and the mixture was stirred for 2.5 hours. To the reaction mixture was added purified water (200 ml) and the aqueous layer was extracted with chloroform (150 ml×3). The combined organic layer was washed succcessively with 5% aqueous hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and saturated aqueous sodium chloride (200 ml), dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was chromatographed over silica gel and the fraction from ethyl acetate-hexane (1/1) gave 19.65 g of 5-hydroxypentyl p-toluenesulfonate. Yield=26%.

1. additionadded at -30° C.
2. additionTo the reaction mixture was added
3. custompurified water (200 ml)
4. extractionthe aqueous layer was extracted with chloroform (150 ml×3)
5. washThe combined organic layer was washed succcessively with 5% aqueous hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and saturated aqueous sodium chloride (200 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off
8. customThe residue was chromatographed over silica gel

ORD record

ord-9b08e092ee1a4721a3de254e59481856

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05736550