Hydroquinone → HCID 18469780, compound

HRID 2228371Notes

Reaction equation

HRID 2228371 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[C:15]([O-:20])(=[O:19])[C:16]([CH3:18])=[CH2:17].[K+].[I-].[K+].C1(C=CC(O)=CC=1)O>>[C:15]([O:20][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

5

Reactant 4

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 18469778HCID 18469778, compoundHCID 23667354Potassium methacrylate

Product 1

HCID 18469780HCID 18469780, compoundYield 86.5%

Conditions

Temperature
100 °C

Procedure

Next, into a flask of 200 ml capacity fitted with a stirrer and cooling tube, there were introduced 15.7 g of 1-(2-chloroethyl)-5-methoxyindole, 18.6 g of potassium methacrylate, 6.2 g of potassium iodide, 40 ml of N,N-dimethylsulfoxide, and a small amount of hydroquinone. They were heated to 100° C., and stirred for 2.5 hours. After completion of the reaction, the insoluble material was removed by infiltration, and concentration was performed under reduced pressure. Further, this reaction mixture was purified by column chromatography using silica gel, to obtain a 16.8 g of 1-(2-methacryloyloxyethyl)-5-methoxyindole.

Workup

  1. customNext, into a flask of 200 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. customAfter completion of the reaction
  4. customthe insoluble material was removed by infiltration, and concentration
  5. customFurther, this reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-eccdf499105147ef9f02d22b064dfedf
Source dataset
uspto-grants-2002_07
Patent number
US06416939B1

Reaction notes

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