Trifluoroacetic acid → 1-Acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane

40.0 g of 1-acetoxy-1-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethane was dissolved in 40 ml of methylene chloride. To the solution was added 80 ml of trifluoroacetic acid with ice cooling. The mixture was stirred for 12 hours at room temperature. After the completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was mixed with 100 ml of toluene. The solvent was further removed by distillation under reduced pressure. The residue thus obtained was dissolved in a mixture of 90 ml of ethanol and 10 ml of water. To the solution was added 10.7 g of sodium hydrogencarbonate at room temperature. The mixture was adjusted to pH 6-7 with a saturated aqueous sodium hydrogencarbonate solution, and then concentrated to about a half volume under reduced pressure. To the concentrate was added 100 ml of ethyl acetate. The organic layer was separated. The aqueous layer was extracted with 50 ml of ethyl acetate. The extract was combined with the previously separated organic layer. The combined organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=3/1) to obtain 19.4 g of oily 1-acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane.

1. customAfter the completion of the reaction
2. customthe solvent was removed by distillation under reduced pressure
3. additionThe residue was mixed with 100 ml of toluene
4. customThe solvent was further removed by distillation under reduced pressure
5. customThe residue thus obtained
6. concentrationconcentrated to about a half volume under reduced pressure
7. additionTo the concentrate was added 100 ml of ethyl acetate
8. customThe organic layer was separated
9. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate
10. washThe combined organic layer was washed with a saturated aqueous sodium chloride solution
11. dry with materialdried over anhydrous magnesium sulfate
12. customThe solvent was removed by distillation under reduced pressure
13. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=3/1)

ORD record

ord-d10b565eb3f84a339bf1aefe32546286

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05872117