4-Toluenesulfonyl chloride → 4-(4-Methylbenzene-1-sulfonyl)butan-2-ol

HRID 610656Notes

Reaction equation

[CH2:1](O)[CH2:2][CH:3]([OH:5])[CH3:4].[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]>C(Cl)Cl>[S:7]([CH2:1][CH2:2][CH:3]([OH:5])[CH3:4])([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1,3-butandiol (1.0 g, 11.1 mmol), Et3 3N (1.6 mL, 11.5 mmol) in CH2Cl2 (10 mL) at 0° C. was added dropwise a solution of TsCl(2.12 g, 11.1 mmol) in CH2Cl3 (5 mL). The resulting mixture was stirred at 0° C. and warmed gradually to room temperature, then kept at room temperature for overnight. It was transferred into a separatory funnel and washed with H2O (3×20 mL). The organic layer was dried (MgSO4), filtered. The filtrate was concentrated in vacuo. The residue was purified on column chromatography (silical gel, 30% ethyl acetate/hexane), thereby affording a colorless oil (1.3 g, 48%). 1H NMR (CDCl3) d 1.07 (d, J=6.0 Hz, 3 H, CH3), 1.52-1.76 (m, 2 H, CH2), 2.33 (s, 3 H, CH3), 3.84 (br s, 1 H, OH), 4.08-4.20 (m, 2 H, CH2), 7.25 (d, J=8.4 Hz, 2 H, aromatic), 7.77 (d, J=8.1 Hz, 2 H, 5 aromatic). 13C NMR (CDCl3) d 21.60 (q, CH3), 23.58 (q, CH3), 37.86 (t, CH2), 64.10 (d, CH), 67.79 (t, CH2OTs), 127.85 (d, aromatic) 129.84 (d, aromatic), 144.78 (s, aromatic), 152.23 (s, aromatic).

Workup

temperaturewarmed gradually to room temperature
customIt was transferred into a separatory funnel
washwashed with H2O (3×20 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified on column chromatography (silical gel, 30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5ca4c352491f41e29f980cc585c199cf
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998624

Reaction notes

Loading…