Sulfuric Acid → HCID 13930749, compound

HRID 542396Notes

Reaction equation

HRID 542396 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:16]=[C:15]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[CH:25]=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-2:27].[O-2:28].[O-2].[Cr+6:30].[S:31](=[O:35])(=[O:34])([OH:33])[OH:32]>CC(C)=O.O>[O-2:14].[O-2:32].[O-2:27].[Cr+6:30].[S:31](=[O:33])(=[O:32])([OH:35])[OH:34].[C:19]1([C:18]#[C:17][C:15]2[CH:16]=[C:9]([C:8]#[C:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:10]([C:25]([OH:27])=[O:26])=[CH:11][C:12]=2[C:13]([OH:28])=[O:14])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 10219390chromium (VI) trioxideHCID 13930748HCID 13930748, compound

Product 2

HCID 13930749HCID 13930749, compoundYield 85.5%HCID 131715098HCID 131715098, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

4,6-Bis(phenylethynyl)isophthalaldehyde (7.8 g, 0.023 mole) was dissolved in acetone (distilled from solid potassium permanganate) and the solution was chilled to 0° C. A chromium trioxide-sulfuric acid solution was prepared by slurrying 26.7 g of chromium trioxide in 23 ml of concentrated sulfuric acid and 40 ml of distilled water. This solution was diluted in the cold with distilled water to 110 ml. A portion of this solution (16.9 ml) was added dropwise over 1.5 hours to the stirred yellow acetone solution. During this period the color of the reaction mixture changed from yellow to brown and finally to green. After an additional 20 hours of reaction, the mixture was warmed to room temperature and poured into a vessel containing ice and water. The yellow precipitate was collected by filtration and washed thoroughly with water. Suction drying on the frit yielded 7.3 g (85.5% yield) of the light yellow 4,6-bis(phenylethynyl)isophthalic acid.

Workup

  1. waitDuring this period the color of the reaction mixture changed
  2. customAfter an additional 20 hours of reaction
  3. temperaturethe mixture was warmed to room temperature
  4. additionpoured into a vessel
  5. filtrationThe yellow precipitate was collected by filtration
  6. washwashed thoroughly with water
  7. customSuction drying on the frit

Sources & evidence

ORD record
ord-fd1b205b1ce04b4da2468f4325640260
Source dataset
uspto-grants-1987_04
Patent number
US04657708

Reaction notes

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