Resorcinol → HCID 59591584, compound

HRID 661732Notes

Reaction equation

HRID 661732 reaction equation
[C:1]12(O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3](O)([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH2:13].[C:14]1([CH3:24])C=CC(S(O)(=O)=O)=[CH:16][CH:15]=1.CO[CH2:27][CH2:28][O:29]C.[C:31]1([CH:38]=[CH:37][CH:36]=[C:34]([OH:35])[CH:33]=1)[OH:32]>O>[OH:32][C:31]1[CH:33]=[C:34]([OH:35])[CH:36]=[CH:37][C:38]=1[C:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]([C:15]4[CH:16]=[CH:27][C:28]([OH:29])=[CH:24][C:14]=4[OH:13])([CH2:8]3)[CH2:2]1)[CH2:4]2

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 80711,2-DimethoxyethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 5738291,3-Adamantanediol

Product 1

HCID 59591584HCID 59591584, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a four-neck flask having an inner volume of 300 ml and equipped with a reflux condenser, a stirrer, a thermometer, and a nitrogen inlet were charged 16.0 g (0.10 mol) of 1,3-adamantanediol, 9.0 g (0.05 mol) of p-toluenesulfonic acid monohydrate, and 20 ml of 1,2-dimethoxyethane. After the atmosphere was displaced by nitrogen, 83.8 g (0.76 mol) of resorcinol was added. The mixture in the flask was placed in an oil bath at 90° C. and agitated for 6 hours. The mixture 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/water mixture solution. The crystals obtained were collected with washing by toluene, and then dried under reduced pressure until constant weight to obtain the target compound (yield 85%).

Workup

  1. customInto a four-neck flask having
  2. customan inner volume of 300 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. temperatureThe mixture was cooled
  6. stirringagitated for 30 minutes
  7. filtrationfiltered
  8. customto obtain a solid material
  9. customThe material was dried under reduced pressure
  10. customrecrystallized from a methanol/water mixture solution
  11. customThe crystals obtained
  12. customwere collected
  13. washwith washing by toluene
  14. customdried under reduced pressure until constant weight

Sources & evidence

ORD record
ord-e94b6553598a4638b3f5ef6525dc7131
Source dataset
uspto-grants-2011_12
Patent number
US08084650B2

Reaction notes

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