Aluminum(III) Chloride → Tetralin

Temperature

-10 °C

1000 g of the sym.-octahydrophenanthrene fraction of Example 1(b) and 250 ml methylene chloride were placed in a stirred flask and cooled to -10° C. Then 40 g of aluminum chloride powder were added in small quantities, while the temperature at times rose to -8° C. The mixture turning darkbrown was uniformly stirred. By crystallization of sym.-octahydroanthracene the addition of further 150 ml methylene chloride was required after about 4 hours. After an additional 2 hours 500 ml of 10 percent sodium hydroxide solution were added for decomposing the aluminum chloride, then the organic phase was separated and after removal of the solvent the organic phase was distilled in vacuum of 12 torr. There resulted in the sequence of the boiling points 5.5 g tetrahydronaphthalene (boiling point 82° C. at 12 torr), 958 g isomer mixture of a boiling point of 167°-168° C. at 12 torr comprising 97 percent sym.-octahydroanthracene and 3 percent sym.-octahydrophenanthrene, as well as a distillation residue of 34.8 g.

1. customrose to -8° C
2. customBy crystallization of sym
3. addition-octahydroanthracene the addition of further 150 ml methylene chloride
4. additionAfter an additional 2 hours 500 ml of 10 percent sodium hydroxide solution were added
5. customthe organic phase was separated
6. customafter removal of the solvent the organic phase
7. distillationwas distilled in vacuum of 12 torr

ORD record

ord-ffcae3490e2540da953bb539168e8211

Source dataset

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04384152