Tyrosol → HCID 86691494, compound

HRID 1482775Notes

Reaction equation

HRID 1482775 reaction equation
[CH:1]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[CH2:11]([C:27](O)=[O:28])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.ClCCCl>[OH:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][C:27]([O:9][CH2:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([OH:10])=[CH:2][CH:1]=3)=[O:28])=[CH:14][CH:15]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10393TyrosolHCID 521998p-Toluenesulfonic acid monohydrateHCID 12444360HCID 12444360, compound

Product 1

HCID 86691494HCID 86691494, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent3×

Procedure

Into a 500 mL round bottomed flask fitted with an overhead stirrer, and a modified Dean-stark trap for solvents heavier than water are added 10 g (72 mmol) of tyrosol, 30 g (78 mmol) of desaminothyronine, 0.65 g (3.4 mmol) of 4-toluenesulfonic acid monohydrate and 200 mL of 1,2-dichloroethane (DCE). A water-cooled reflux condenser is placed on top of the modified Dean-stark trap and the contents of the flask are heated to reflux while being stirred. The reaction is continued until approximately 1.4 mL of water collected in the modified Dean-stark trap above the DCE and the water collection essentially stops (about 4 hours of reflux). The reaction mixture is cooled to room temperature and the crude product is dissolved in 100 mL of ethyl acetate and washed twice with 100 mL portions of 5% sodium bicarbonate solution. After drying over magnesium sulfate the organic layer is concentrated and precipitated with hexane. The resulting white crystalline solid is collected by filtration and dried in a vacuum oven at 25° C. The product is characterized by elemental analysis, hplc, and 1H NMR.

Workup

  1. temperaturereflux condenser
  2. temperaturethe contents of the flask are heated
  3. temperatureto reflux
  4. customcollected in the modified Dean-stark trap above the DCE
  5. customthe water collection
  6. temperature(about 4 hours of reflux)
  7. dissolutionthe crude product is dissolved in 100 mL of ethyl acetate
  8. washwashed twice with 100 mL portions of 5% sodium bicarbonate solution
  9. dry with materialAfter drying over magnesium sulfate the organic layer
  10. concentrationis concentrated
  11. customprecipitated with hexane
  12. filtrationThe resulting white crystalline solid is collected by filtration
  13. customdried in a vacuum oven at 25° C

Sources & evidence

ORD record
ord-7f0f76cb4b574d6cb1abb358f3b0adbb
Source dataset
uspto-grants-2016_08
Patent number
US09416090B2

Reaction notes

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