Water → HCID 4855228, compound

HRID 1249109Notes

Reaction equation

HRID 1249109 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.Cl[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1.C(=O)([O-])[O-:44].[K+].[K+].O>CS(C)=O>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:44][C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 4855228HCID 4855228, compoundYield 126.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 50 ml of dimethylsulfoxide, 12 g of hydroquinone monobenzyl ether, 8.2 g of 2-chloroquinoline and 8.3 g of potassium carbonate were dissolved and the mixture was heated at 150° to 160° C. for 4 hours to react them. After cooling, the reaction mixture was poured into water and the product was extracted with ether for several times and the ether layer was washed with an aqueous solution of sodium hydroxide and then with water and the ether layer was dehydrated over sodium sulfate. The solvent was distilled off. The resulting crude crystal was washed with diisopropyl ether to obtain 12 g (yield 75%) of 2-(4-benzyloxyphenoxy)quinoline. All of the intermediate was dissolved in 200 ml of a mixed solvent of tetrahydrofuran and ethanol (5:1) and 1.5 g of palladium-carbon type catalyst was added and 880 ml of hydrogen gas was fed into the mixture to carry out the hydrogenation at the atmospheric pressure. After the hydrogenation, the catalyst was separated by a suction filtration and the solvent was distilled off and the residue was washed with chloroform-n-hexane type solvent to obtain 6.3 g (yield 74%) of white crystal of 2-(4-hydroxyphenoxy)quinoline (m.p. 177° C.).

Workup

  1. temperaturethe mixture was heated at 150° to 160° C. for 4 hours
  2. customto react them
  3. temperatureAfter cooling
  4. extractionthe product was extracted with ether for several times
  5. washthe ether layer was washed with an aqueous solution of sodium hydroxide
  6. distillationThe solvent was distilled off
  7. washThe resulting crude crystal was washed with diisopropyl ether

Sources & evidence

ORD record
ord-3ca6520aa099497197d13803facd82d8
Source dataset
uspto-grants-1986_12
Patent number
US04629493

Reaction notes

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