Hydrochloric Acid → Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)

HRID 842422Notes

Reaction equation

HRID 842422 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].N1C=CC=CC=1.[CH3:18][O:19][CH2:20][CH2:21][OH:22].Cl>CN(C1C=CN=CC=1)C.ClCCl>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O:22][CH2:21][CH2:20][O:19][CH3:18])(=[O:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 80192-Methoxyethanol

Product 1

HCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)Yield 85.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To tosyl chloride (50.0 g, 0.263 mol) at 0° C. and under nitrogen were added anhydrous dichloromethane (80 ml), anhydrous pyridine (23 ml, 24.3 g, 0.29 mol), 2-methoxyethanol (21.0 ml, 20.0 g, 0.263 mol) and a catalytic quantity of DMAP. After 10 minutes the mixture was warmed to room temperature, at which it was stirred for 16 hours. Dichloromethane (100 ml) and 1 M aqueous hydrochloric acid (50 ml) were added. The organic layer was isolated and washed with 1 M aqueous hydrochloric acid (4×30 ml) and water (4×30 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound (51.68 g, 85%) as an oil.

Workup

  1. customThe organic layer was isolated
  2. washwashed with 1 M aqueous hydrochloric acid (4×30 ml) and water (4×30 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21a97204e59b437e8661132fca9ed035
Source dataset
uspto-grants-2002_04
Patent number
US06375926B1

Reaction notes

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