Carbon Dioxide → 103986-80-7

Temperature

145 °C

A mixture of 5,6,7,8-tetrahydro-1-naphthol (7.42 g, 50 mmol) and potassium carbonate (25.5 g, 185 mmol) were placed in a glass tube inside a stainless steel pressure reactor. The reactor was charged with CO2 at 40 bar and then heated to 145° C. The pressure rose to 60 bar and then slowly dropped to 20 bar over the 3 day reaction period. The bomb was cooled and the solid product was taken up in water (˜500 ml) and acetone (˜500 ml). The mixture was evaporated in vacuo to remove the acetone and then washed with DCM (3×150 ml). The aqueous was acidified with 2M hydrochloric acid to give a white suspension. This was extracted with DCM (4×250 ml), which was then dried over sodium sulphate and evaporated in vacuo to give the crude product. This was recrystallised from aqueous ethanol and dried under high vacuum to provide 8.64 g (45 mmol, 90% yield) of the title compound as a pale brown powder. 1H NMR (200 MHz., d6-DMSO) δ 1.81 (4H, m); 2.67 (2H, m); 2.81 (2H, m); 6.73 (1H, d); 7.61 (1H, d); 11.78 (1H, bs). EIMS m/z=192 (M+); 174; 146

1. customwere placed in a glass tube inside a stainless steel pressure reactor
2. additionslowly dropped to 20 bar over the 3 day reaction period
3. temperatureThe bomb was cooled
4. customThe mixture was evaporated in vacuo
5. customto remove the acetone
6. washwashed with DCM (3×150 ml)
7. customto give a white suspension
8. extractionThis was extracted with DCM (4×250 ml), which
9. dry with materialwas then dried over sodium sulphate
10. customevaporated in vacuo
11. customto give the crude product
12. customThis was recrystallised from aqueous ethanol
13. customdried under high vacuum

ORD record

ord-856bb4c6f4864f9b807dc9973e799930

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674823B2