Water → HCID 21122251, compound

Temperature

130 °C

Titanium(IV) chloride (7.89 g, 41.6 mmol) was dissolved in 1,2-dichloroethane (30 ml). To this solution was added dropwise at room temperature the solution of phenyl 3-phenylbutanoate (10 g, 41.6 mmol) in 1,2-dichloroethane (20 ml). The resulting dark brown solution was heated to 130° C. for 6 h, then cooled to 90° C. and toluene (40 ml) was added. The mixture was cooled to 5° C. and water (40 ml) was added carefully to keep the temperature below 10° C. The mixture was then transferred into a separatory funnel, the phases separated and the organic layer washed twice with water, then twice with 1 N aq. NaOH-solution (100 ml), followed by six washes with half saturated brine. The organic layer was dried with MgSO4 and the solvent removed in a rotary evaporator and the residue thoroughly dried to yield 3.82 g (38%) of a dark oil, which was bulb-to-bulb distilled at 170-180° C./0.05 mbar to yield 1.74 g (17%), which was further purified by column flash chromatography on silica to obtain 1.2 g (12%) of product, which was finally recrystallized from hexane/toluene 2:1 to yield 1.1 g (11%) of product as white crystals, melting point 76.8° C.

1. temperaturecooled to 90° C.
2. temperatureThe mixture was cooled to 5° C.
3. customthe temperature below 10° C
4. customThe mixture was then transferred into a separatory funnel
5. customthe phases separated
6. washthe organic layer washed twice with water
7. dry with materialThe organic layer was dried with MgSO4
8. customthe solvent removed in a rotary evaporator
9. customthe residue thoroughly dried

ORD record

ord-eb39615cab6642a0a9d43a2617ba0ca9

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877704B2