Water → HCID 87333398, compound

HRID 249636Notes

Reaction equation

HRID 249636 reaction equation
FC(F)(F)[C:3](O)=[O:4].[CH2:8]1N2CN3CN(C2)CN1C3.[CH3:18][C:19]1[CH:24]=[C:23](O)[CH:22]=[CH:21][C:20]=1[C:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][C:28]([C:36]4[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][C:37]=4[CH3:43])([CH2:29]3)[CH2:27]1)[CH2:33]2.[OH-:44].[Na+].[OH2:46]>C(OCC)(=O)C>[CH:18]([C:19]1[CH:24]=[C:23]([OH:46])[CH:22]=[C:21]([CH3:8])[C:20]=1[C:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][C:28]([C:36]4[C:37]([CH3:43])=[CH:38][C:39]([OH:42])=[CH:40][C:41]=4[CH:3]=[O:4])([CH2:29]3)[CH2:27]1)[CH2:33]2)=[O:44]

Participants

7

Reactant 5

HCID 962Water2×HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22731501HCID 22731501, compound

Product 1

HCID 87333398HCID 87333398, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
90 °C

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).

Workup

  1. additionmixed at room temperature over 1 hour
  2. customat 70° C.
  3. customover 1 hour
  4. additionwas added at 70° C.
  5. stirringby stirring for 2 hours and 30 minutes
  6. temperaturewhile maintaining
  7. stirringthe temperature (wherein crystals were deposited while stirring)
  8. temperatureThereafter, the resultant was cooled
  9. customwas elevated to 60° C.
  10. temperaturecooled
  11. filtrationThen, the resultant was filtered
  12. customto obtain 126.8 g of crude crystals
  13. additionwere charged into a 2-L four-necked flask
  14. customwas elevated to 70° C.
  15. waitto stand for 10 minutes
  16. customby removing the water layer
  17. additionThen, 100 g of water was added
  18. customwater washing and liquid separation
  19. concentrationThereafter, the resultant was concentrated under reduced pressure
  20. customto remove 962.3 g of the solvent (wherein crystals
  21. concentrationwere deposited during the concentration)
  22. temperatureThe resulting concentrated product was cooled to 23° C.
  23. filtrationfollowed by filtration
  24. customdrying

Sources & evidence

ORD record
ord-35783ed144b5411ca5634289c91bee7e
Source dataset
uspto-grants-2011_01
Patent number
US07862981B2

Reaction notes

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