Sulfuric Acid → HCID 19928698, compound

In a 1 L flask equipped with a stirrer, a reflux condenser and a dropping funnel, a mixture of 50 g (0.33 M) 1-adamantanol, 68 g (45.5 mL, 0.36 M) 4-bromoanisole and 500 mL of methylene chloride is prepared. The mixture is stirred until dissolved and then 35 g (19 mL, 0.36 M) sulfuric acid added during one hour. The reaction mixture is stirred for 4 hours, 200 mL of water added, stirred for another 10 min, transferred to separating funnel and the organic layer collected, which is neutralized by two portions of 100 mL 10% sodium carbonate solution. Methylene chloride is distilled off completely, the residue dissolved in 300 mL of ethyl acetate, filtered, concentrated to 200 mL and left to crystallize at 0° C. for 16 h. The crystals are filtered off, washed by 50 mL of cold ethyl acetate and dried at 100° C. for one hour. 2-adamantyl-4-bromoanisole, 76 g (72%) with m.p. 140-141° C. is obtained.

1. customIn a 1 L flask equipped with a stirrer, a reflux condenser and a dropping funnel
2. customis prepared
3. dissolutionuntil dissolved
4. stirringThe reaction mixture is stirred for 4 hours
5. stirringstirred for another 10 min
6. customto separating funnel
7. customthe organic layer collected
8. distillationMethylene chloride is distilled off completely
9. dissolutionthe residue dissolved in 300 mL of ethyl acetate
10. filtrationfiltered
11. concentrationconcentrated to 200 mL
12. waitleft
13. customto crystallize at 0° C. for 16 h
14. filtrationThe crystals are filtered off
15. washwashed by 50 mL of cold ethyl acetate
16. customdried at 100° C. for one hour

ORD record

ord-cae8ecdbe40f43d3ab4280adbab8a55d

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119835B2