Boron trifluoride etherate → 1-(2,4-Dihydroxy-5-isopropylphenyl)ethanone

4-Isopropyl-benzene-1,3-dial (5.8 g) and boron trifluoride etherate (28.7 ml) were introduced into a 250 ml single neck RB flask equipped with a reflux condenser and an inlet for nitrogen atmosphere stirred at room temperature for 10 minutes. Acetic acid (4.55 ml) was added to the reaction mixture and stirred at 90° C. for 16 hours. On completion, 10% sodium acetate (300 ml) was added to the reaction mixture which was stirred at room temperature for 4 hours. The reaction mixture was then extracted with ethyl acetate (300 ml) and washed with saturated sodium bicarbonate (100 ml) and the organic layer was dried over sodium sulphate. The reaction was monitored by TLC (10% EtOAc/n-hexane, product Rf˜0.5). The solvent was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, 10% EtOAc/n-hexane).

1. customequipped with a reflux condenser and an inlet for nitrogen atmosphere
2. stirringstirred at 90° C. for 16 hours
3. stirringwas stirred at room temperature for 4 hours
4. extractionThe reaction mixture was then extracted with ethyl acetate (300 ml)
5. washwashed with saturated sodium bicarbonate (100 ml)
6. dry with materialthe organic layer was dried over sodium sulphate
7. customThe solvent was removed under reduced pressure
8. customto give a residue, which
9. customwas further purified by column chromatography (SiO2, 10% EtOAc/n-hexane)

ORD record

ord-8991e50d91764fa3a5075cea009633d0

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08779132B2