Reaction #336818

Reaction equation

trifluoroacetic acid

1,3-bis(2-methyl-4-hydroxyphenyl)-adamantane

sodium hydroxide

water

hexamethylenetetramine

water

→

object product

Yield 56.3%

1,3-bis(2-formyl-6-methyl-4-hydroxyphenyl)-adamantane

Yield 56.3%

Solvents

ethyl acetate

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONmixed at room temperature over 1 hour
2. 2
   Otherat 70° C.
3. 3
   Otherover 1 hour
4. 4
   workup.ADDITIONwas added at 70° C.
5. 5
   workup.STIRRINGby stirring for 2 hours and 30 minutes
6. 6
   Temperaturewhile maintaining
7. 7
   workup.STIRRINGthe temperature (wherein crystals were deposited while stirring)
8. 8
   TemperatureThereafter, the resultant was cooled
9. 9
   Otherwas elevated to 60° C.
10. 10
    Temperaturecooled
11. 11
    FiltrationThen, the resultant was filtered
12. 12
    Otherto obtain 126.8 g of crude crystals
13. 13
    workup.ADDITIONwere charged into a 2-L four-necked flask
14. 14
    Otherwas elevated to 70° C.
15. 15
    workup.WAITto stand for 10 minutes
16. 16
    Otherby removing the water layer
17. 17
    workup.ADDITIONThen, 100 g of water was added
18. 18
    Otherwater washing and liquid separation
19. 19
    ConcentrationThereafter, the resultant was concentrated under reduced pressure
20. 20
    Otherto remove 962.3 g of the solvent (wherein crystals
21. 21
    Concentrationwere deposited during the concentration)
22. 22
    TemperatureThe resulting concentrated product was cooled to 23° C.
23. 23
    Filtrationfollowed by filtration
24. 24
    Otherdrying

Procedure

In a 2-L four-necked flask, 615.6 g (5.4 mol) of trifluoroacetic acid was measured, and 126.0 g (0.9 mol) of hexamethylenetetramine was dropwise added and mixed at room temperature over 1 hour. Then, to the resulting mixture was intermittently added 104.4 g (0.3 mol) of 1,3-bis(2-methyl-4-hydroxyphenyl)-adamantane in the form of a powder at 70° C. over 1 hour, followed by stirring at 90° C. for 25 hours. Then, to the resulting reaction mixture, 210.0 g of water was added at 70° C., followed by stirring for 2 hours and 30 minutes while maintaining the temperature (wherein crystals were deposited while stirring). Thereafter, the resultant was cooled and neutralized with 16% by weight aqueous solution of sodium hydroxide. The neutralized liquid was elevated to 60° C., and 100 g of ethyl acetate was added thereto and cooled. Then, the resultant was filtered to obtain 126.8 g of crude crystals. Subsequently, the obtained crude crystals, 1,204.6 g of ethyl acetate and 150 g of water were charged into a 2-L four-necked flask, and the content of the flask was elevated to 70° C. and melted. Then, the resultant was allowed to stand for 10 minutes, followed by removing the water layer. Then, 100 g of water was added, and water washing and liquid separation were performed in the same manner. Thereafter, the resultant was concentrated under reduced pressure to remove 962.3 g of the solvent (wherein crystals were deposited during the concentration). The resulting concentrated product was cooled to 23° C., followed by filtration and drying, thereby obtaining 68.2 g of an object product which was a pale yellow powder (yield: 56.3%, based on 1,3-bis(2-methyl-4-hydroxyphenyl)adamantane).

Source