Hydrochloric Acid → 1-Indanone-6-carboxylic acid

Temperature

190 °C

A mixture of 4-(2-carboxyethyl)benzoic acid (20.0 g, 103.09 mmol, 1.0 eq.), AlCl3 (164.0 g, 1237.11 mmol, 12.0 eq.) and NaCl (16.4 g, 10% mass weight of AlCl3) was heated for 12 hours at 190° C. The mixture was poured onto ice (500 g), and 6 M HCl (500 ml) and ethyl acetate (800 ml) were added. The phases were separated and the aqueous phase was extracted with ethyl acetate (3×400 ml). The combined org. phases were washed with 2 M HCl solution (2×400 ml), water (2×400 ml) and sat. NaCl solution (500 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was used in the next stage without being purified further. Yield: 77% (14.0 g, 79.545 mmol)

1. additionwere added
2. customThe phases were separated
3. extractionthe aqueous phase was extracted with ethyl acetate (3×400 ml)
4. washphases were washed with 2 M HCl solution (2×400 ml), water (2×400 ml) and sat. NaCl solution (500 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customwithout being purified further

ORD record

ord-e1d8e1c163654f52b5b934a5ac652624

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680159B2