Ethanol → Ethyl 4-benzyloxyphenethyl sulfonate

HRID 1488338Notes

Reaction equation

HRID 1488338 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][CH2:14][S:15]([O-:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].CN(C)C=O.S(Cl)(Cl)=O.[CH2:31](O)[CH3:32]>C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][CH2:14][S:15]([O:18][CH2:31][CH3:32])(=[O:16])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86751366Sodium 4-benzyloxyphenethyl sulfonate

Product 1

HCID 22904628Ethyl 4-benzyloxyphenethyl sulfonate

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of sodium 4-benzyloxyphenethyl sulfonate (4.84 g) and dimethylformamide (0.5 ml) in toluene (40 ml) is added dropwise thionyl chloride (1.35 ml) and the mixture heated at 90° C. for about 5 hours. The mixture is cooled to room temperature and is added portionwise to a solution of absolute ethanol (30 ml) and pyridine (15 ml) at -20° C. The mixture is stirred for 5 hours while being allowed to warm to 0° C. The mixture is diluted with ethyl acetate and 10% aqueous hydrochloric acid. The organic layer is washed with dilute HCl, water, saturated sodium bicarbonate solution, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give ethyl 4-benzyloxyphenethyl sulfonate.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. temperatureto warm to 0° C
  3. washThe organic layer is washed with dilute HCl, water, saturated sodium bicarbonate solution, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25c42dab8ab6404894b35bf85b14365c
Source dataset
uspto-grants-1997_10
Patent number
US05674482

Reaction notes

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