Pyridine → Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)

HRID 2061783Notes

Reaction equation

HRID 2061783 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[CH:19]([OH:21])[CH3:20].[Cl:22]CCl>>[Cl:22][CH2:20][CH2:19][O:21][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 126390351-Chloroethan-1-ol

Product 1

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)Yield 100%

Procedure

p-Toluenesulfonyl chloride (172 g, 0.884 mol) and pyridine (59 g, 0.75 mol) were added to 180 mL dichloromethane (DCM) in a 1 L round-bottom flask (RBF) which was placed in an ice bath for ca. 5 min. 1-Chloroethanol (40.3 g, 0.496 mol) was added slowly, and the RBF was taken out of the ice bath and left to stir at room temperature (r.t.) for 15 hrs. The reaction mixture was poured into a 1 L separatory funnel, washed twice with 300 mL water+50 mL pyridine, and again with 300 mL water+75 mL 36% wt aq. HCl (discarding the aqueous phase after each wash). Removal of the solvent at reduced pressure yielded analytically pure 1 as a faint yellow, thick syrup (116 g, 0.494 mol, 100% yield). 1H NMR: δ=7.81 (d, 2 aromatic H meta to CH3, J=8.3 Hz), 7.37 (d, 2 aromatic H ortho to CH3, J=8.3 Hz), 4.23 (t, OCH2, J=5.9 Hz), 3.66 (t, CH2Cl, J=5.9 Hz), 2.46 (s, CH3).

Workup

  1. waitleft
  2. additionThe reaction mixture was poured into a 1 L separatory funnel
  3. washwashed twice with 300 mL water+50 mL pyridine
  4. washeach wash)
  5. customRemoval of the solvent at reduced pressure

Sources & evidence

ORD record
ord-8dc6575541fc413ab53bddf75dfc1578
Source dataset
uspto-grants-2012_10
Patent number
US08283438B2

Reaction notes

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