Potassium Hydroxide → HCID 88769560, compound

HRID 1659556Notes

Reaction equation

HRID 1659556 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:12]([CH3:13])[C:11]3[CH:14]=[C:15](/[CH:20]=[CH:21]/[CH3:22])[CH:16]=[C:17]([O:18][CH3:19])[C:10]=3[O:9]2)=[CH:4][C:3]=1[O:23][CH3:24].Cl.[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28].[OH-].[K+]>C1(C)C=CC=CC=1>[CH3:19][O:18][C:17]1[C:10]2[O:9][C@@H:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][CH2:30][CH2:29][N:27]([CH3:28])[CH3:26])=[C:3]([O:23][CH3:24])[CH:4]=3)[C@H:12]([CH3:13])[C:11]=2[CH:14]=[C:15](/[CH:20]=[CH:21]/[CH3:22])[CH:16]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 6442393(-)-Licarin AHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 88769560HCID 88769560, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15 g of trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofurane("Dehydrodiisoeugenol") are dissolved in 150 ml abs. toluene at 80° . 9.5 g of N,N-dimethyl-2-chloroethylamine-hydrochloride and 15.5 g KOH in solid form are added. After 6 h at 80°, the solution is cooled down and decanted from solid KOH, whereafter the toluene solution is washed with water to remove dissolved KOH. After drying over sodium sulfate, the solution is evaporated in vacuo. The residue is cristallized in vacuo, and the still present non-cristalline part is dissolved in petroleum ether. One obtains 11.2 g of N-2-[4-(trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenylbenzofurane-2-yl)-2-methoxyphenoxy]ethyl-N,N,-dimethylamine, as slightly yellow cristals of mp 58°-60° C.

Workup

  1. customat 80°
  2. temperaturethe solution is cooled down
  3. customdecanted from solid KOH, whereafter the toluene solution
  4. washis washed with water
  5. customto remove
  6. dissolutiondissolved KOH
  7. dry with materialAfter drying over sodium sulfate
  8. customthe solution is evaporated in vacuo
  9. dissolutionthe still present non-cristalline part is dissolved in petroleum ether

Sources & evidence

ORD record
ord-78b96d42317041b09f3adc716fe86179
Source dataset
uspto-grants-1981_12
Patent number
US04304785

Reaction notes

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