1,4-Cyclohexanedione → HCID 66749276, compound

HRID 625197Notes

Reaction equation

HRID 625197 reaction equation
[I:1][C:2]1[S:6][C:5]([CH:7]=O)=[C:4]([CH:9]=O)[CH:3]=1.[C:11]1(=[O:18])[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[OH-].[K+]>>[I:1][C:2]1[S:6][C:5]2[CH:7]=[C:15]3[C:14](=[O:17])[C:13]4[C:12](=[CH:9][C:4]5[CH:3]=[C:2]([I:1])[S:6][C:5]=5[CH:7]=4)[C:11](=[O:18])[C:16]3=[CH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 125111,4-CyclohexanedioneHCID 14797Potassium HydroxideHCID 77230807HCID 77230807, compound

Product 1

HCID 66749276HCID 66749276, compoundYield 87%

Conditions

Temperature
20 °C

Procedure

5-Iodo-2,3-thiophenedicarboxaldehyde (20.00 g, 75.15 mmol) and 1,4-cyclohexandione (4.25 g, 37.12 mmol) were dissoved in IMS (industrial methylated spirits) (600 cm3) by warming and stirring, and then cooled to 20° C. with a water bath. 5% KOH solution (7.5 cm3) was added in one portion under nitrogen with vigorous stirring. The reaction mixture was stirred at 20° C. for 30 minutes and the precipitate formed was collected by suction filtration, washed with IMS, water, IMS, then acetone, and dried in the vacuum oven at 40° C. overnight to yield 2,8-diiodo-anthra[2,3-b:7,6-b′]dithiophene-5,11-dione (18.39 g, 87%). The solid was directly used for the following reactions without further purification.

Workup

  1. temperatureby warming
  2. stirringThe reaction mixture was stirred at 20° C. for 30 minutes
  3. customthe precipitate formed
  4. filtrationwas collected by suction filtration
  5. washwashed with IMS, water, IMS
  6. dry with materialacetone, and dried in the vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-9890c666390b494382866c53b301456e
Source dataset
uspto-grants-2016_04
Patent number
US09306172B2

Reaction notes

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