Reaction #1973933

Reaction equation

3-methyl-1,3-butane diol

p-(trifluoromethyl)benzenesulfonyl chloride

HCl

→

solid

Yield 71.1%

3-Hydroxy-3-methylbutyl 4-(trifluoromethyl)benzenesulfonate

Yield 71.1%

Solvents

pyridine

ethyl acetate

pyridine

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic phase was washed with HCl (4×50 mL, 2 N), brine (1×25 mL)
3. 3
   Dryingdried over MgSO4
4. 4
   Otherevaporated to dryness
5. 5
   OtherRepeat synthesis
6. 6
   workup.STIRRINGThe solution was stirred at 0° C. for 2 h
7. 7
   Washwashed with 1 M HCl (3×50 mL), saturated aqueous NaHCO3 (1×50 mL) and saturated aqueous NaCl (1×50 mL)
8. 8
   DryingThe organics were dried over Na2SO4
9. 9
   Concentrationconcentrated

Procedure

A mixture of 3-methyl-1,3-methanebutane diol (2.00 g, 19.2 mmol), (4-trifluoromethyl)benzene sulfonyl chloride (7.046 g, 28.8 mmol) in dry pyridine (20 mL) was stirred at 0° C. for 2 hours, poured into the cold HCl (50 mL, 2 N), and extracted with ethyl acetate. The organic phase was washed with HCl (4×50 mL, 2 N), brine (1×25 mL), dried over MgSO4, and evaporated to dryness. (3.72 g, 97%). 1H NMR (400 MHz, CDCl3): δ 1.21 (s, 6H), 1.87 (t, J=6.9, 2H), 2.03 (d, J=14.0, 2H), 4.26 (t, J=6.9, 2H), 7.81 (d, J=8.6, 2H), 8.03 (d, J=8.1, 2H). Repeat synthesis: To a solution of 3-methyl-1,3-butane diol (1.9 g, 18.2 mmol) in pyridine (15 mL) was added p-(trifluoromethyl)benzenesulfonyl chloride (3.67 g, 15 mmol). The solution was stirred at 0° C. for 2 h. The reaction mixture was diluted with ethyl acetate (40 mL) and washed with 1 M HCl (3×50 mL), saturated aqueous NaHCO3 (1×50 mL) and saturated aqueous NaCl (1×50 mL). The organics were dried over Na2SO4 and concentrated to give a white low melting point solid (3.33 g, 71%). 1H NMR (400 MHz CDCl3) δ 8.04 (d, 2H, J=8.0 Hz), 7.81 (d, 2H, J=8.0 Hz), 4.72 (t, 2H, J=7.0 Hz), 1.87 (t, 2H, J=7.0 Hz), 1.21 (s, 6H). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 46.14; H, 4.90.

Source