Resorcinol → HCID 57552322, compound

HRID 1169541Notes

Reaction equation

HRID 1169541 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH3:10])[CH2:4][CH:3]1[C:11]([O:13][CH3:14])=[O:12].C1([CH:22]=[CH:21][CH:20]=[C:18]([OH:19])[CH:17]=1)O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[CH2:34](I)[CH3:35]>C1(C)C=CC=CC=1.O>[CH2:34]([O:19][C:18]1[CH:17]=[C:14]2[C:22]([C:2]3[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH3:10])[CH2:4][C:3]=3[C:11](=[O:12])[O:13]2)=[CH:21][CH:20]=1)[CH3:35]

Participants

8

Reactant 5

HCID 5054ResorcinolHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 59550428HCID 59550428, compound

Product 1

HCID 57552322HCID 57552322, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

16.6 g (78.5 mmol) of methyl 2-oxo-5-propylcyclohexanecarboxylate, 7.65 g (69.5 mmol) of resorcinol and 5.6 ml (6.1 mmol) of phosphoryl chloride are dissolved in 55 ml of toluene, and the mixture is heated under reflux for 3 h. After hydrolysis using water, the deposited precipitate is filtered off with suction, washed with toluene and dried. The product is dissolved in 200 ml of acetone, 20 g (145 mmol) of potassium carbonate and 9.00 g (57.7 mmol) of ethyl iodide are added, and the mixture is heated under reflux for 5 h. The majority of the solvent is removed under reduced pressure, and the residue is taken up in MTB ether/water. The aqueous phase is separated off and extracted with MTB ether. The combined organic phases are washed with water and dried over sodium sulfate. The solvent is removed under reduced pressure, and the crude product is recrystallised from ethanol, giving 3-ethoxy-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one as colourless crystals. The melting point is 108° C. The other physical properties are: Δ∈=−7.5 (extrapolated from 5% solution in ZLI-2857), Δn=0.1302 (5% in ZLI-4792).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 h
  3. customAfter hydrolysis
  4. filtrationthe deposited precipitate is filtered off with suction
  5. washwashed with toluene
  6. customdried
  7. dissolutionThe product is dissolved in 200 ml of acetone
  8. temperaturethe mixture is heated
  9. temperatureunder reflux for 5 h
  10. customThe majority of the solvent is removed under reduced pressure
  11. customThe aqueous phase is separated off
  12. extractionextracted with MTB ether
  13. washThe combined organic phases are washed with water
  14. dry with materialdried over sodium sulfate
  15. customThe solvent is removed under reduced pressure
  16. customthe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-3d322a73b98d45699bdee5ef9869b9d5
Source dataset
uspto-grants-2010_11
Patent number
US07824745B2

Reaction notes

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