Ethanol → HCID 15105171, compound

HRID 661730Notes

Reaction equation

HRID 661730 reaction equation
[C:1]12(O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C.[C:27]1([CH:34]=[CH:33][CH:32]=[C:30]([OH:31])[CH:29]=1)[OH:28]>O>[OH:28][C:27]1[CH:29]=[C:30]([OH:31])[CH:32]=[CH:33][C:34]=1[C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 702EthanolHCID 5054ResorcinolHCID 641521-AdamantanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 15105171HCID 15105171, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a four-neck flask having an inner volume of 500 ml and equipped with a reflux condenser, a stirrer, a thermometer, and a nitrogen inlet were charged 28.1 g (0.18 mol) of 1-adamantanol, 8.8 g (0.05 mol) of p-toluenesulfonic acid monohydrate, and 35 ml of ethanol. After the atmosphere was displaced by nitrogen, 39.6 g (0.36 mol) of resorcinol was added. The mixture in the flask was placed in an oil bath at 90° C. and heated and agitated for 3 hours. The reaction solution was cooled, added with 200 ml of pure water, agitated for 30 minutes, and then filtered to obtain a solid material. The material was dried under reduced pressure, then recrystallized from a methanol/toluene mixture solvent. The crystals obtained were collected with washing by toluene, and then dried under reduced pressure until constant weight to obtain the target compound (yield 86%).

Workup

  1. customInto a four-neck flask having
  2. customan inner volume of 500 ml and equipped with a reflux condenser, a stirrer
  3. additionwas added
  4. customThe mixture in the flask was placed in an oil bath at 90° C.
  5. temperatureheated
  6. temperatureThe reaction solution was cooled
  7. stirringagitated for 30 minutes
  8. filtrationfiltered
  9. customto obtain a solid material
  10. customThe material was dried under reduced pressure
  11. customrecrystallized from a methanol/toluene mixture solvent
  12. customThe crystals obtained
  13. customwere collected
  14. washwith washing by toluene
  15. customdried under reduced pressure until constant weight

Sources & evidence

ORD record
ord-1f285654fa9a4c24a1ea4a47a6f44e75
Source dataset
uspto-grants-2011_12
Patent number
US08084650B2

Reaction notes

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