Hydrochloric Acid → 1(1Naphthyl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol

HRID 862518Notes

Reaction equation

HRID 862518 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[OH:7].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.Cl.C(OCC)C>N1C=CC=CC=1>[C:8]1([CH:6]([OH:7])[CH2:5][O:4][CH2:3][CH2:2][O:1][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 538852792-(2-Hydroxyethoxy)-1-(1-naphthyl)ethanol

Product 1

HCID 541300371(1Naphthyl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-25 °C

Procedure

8.3 g of 2-(2-hydroxyethoxy)-1-(1-naphthyl)ethanol was dissolved in 50 ml of pyridine. The solution was cooled to -25° C. Thereto was added 6.8 g of p-toluenesulfonyl chloride. The resulting mixture was allowed to stand at 0°-5° C. for 24 hours and further at room temperature for 4 hours. The reaction mixture was added to a mixture of 103 ml of 6N hydrochloric acid, 50 ml of ice water and 100 ml of diethyl ether. The resulting mixture was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated. The aqueous layer was extracted with 20 ml of diethyl ether. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=10/1) to obtain 6.3 g of colorless, oily 1-(1-naphthyl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol.

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with 20 ml of diethyl ether
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (eluant: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-dfa39a0f0a2b48b09ff50688a3d83010
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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