Water → HCID 12812398, compound

A solution of 9.95 g of 5-chloro-2-hydroxy-α-methyl-α-phenyl-benzene-methanol in 150 ml of anhydrous toluene was added dropwise at room temperature to a mixture of 4 g of sodium amide and 50 ml of anhydrous toluene and the mixture was refluxed for 6 hours and cooled to room temperature. 10.25 g of potassium dibromoacetate were added thereto and the mixture was refluxed for another 6 hours and cooled. 200 ml of water were added thereto and the organic phase was decanted and extracted twice with 80 ml of water. The aqueous phase was washed twice with 80 ml of ether and was acidified with 40 ml of 2 N hydrochloric acid. The resulting precipitate was extracted 3 times with 100 ml of ether and the ether extracts were washed twice with 80 ml of water and extracted with 50% of an aqueous 5% sodium bicarbonate solution. The aqueous phase was washed 3 times with 80 ml of ether and acidified with 90 ml of 2 N hydrochloric acid solution. The mixture was extracted 4 times with 100 ml of ether and the combined ether extracts were washed with water, dried over magnesium sulfate, treated with activated carbon and evaporated to dryness under reduced pressure to obtain 7.85 g of raw product. The latter was taken up in hexane and vacuum filtered and the recovered crystals were dried to obtain 6 g of 6-chloro-4-methyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of two racemates diastereoisomers) melting at 144° C.

1. temperaturethe mixture was refluxed for 6 hours
2. temperaturethe mixture was refluxed for another 6 hours
3. temperaturecooled
4. customthe organic phase was decanted
5. extractionextracted twice with 80 ml of water
6. washThe aqueous phase was washed twice with 80 ml of ether
7. extractionThe resulting precipitate was extracted 3 times with 100 ml of ether
8. washthe ether extracts were washed twice with 80 ml of water
9. extractionextracted with 50% of an aqueous 5% sodium bicarbonate solution
10. washThe aqueous phase was washed 3 times with 80 ml of ether
11. extractionThe mixture was extracted 4 times with 100 ml of ether
12. washthe combined ether extracts were washed with water
13. dry with materialdried over magnesium sulfate
14. additiontreated with activated carbon
15. customevaporated to dryness under reduced pressure
16. customto obtain 7.85 g of raw product
17. filtrationvacuum filtered
18. customthe recovered crystals were dried

ORD record

ord-a9343b257fe746baaa9a62a40e52306c

Source dataset

uspto-grants-1981_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04294845