Sulfuric Acid → HCID 13753879, compound

HRID 652512Notes

Reaction equation

HRID 652512 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH:14]=[O:15])=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:23]>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:14]([OH:23])=[O:15])=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13753878HCID 13753878, compound

Product 1

HCID 13753879HCID 13753879, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

To 0.58 g of chromium trioxide in 8 ml of 10N sulfuric acid cooled at 0° was added a solution of 1.51 g of 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hexynal in 15 ml of acetone over 30 minutes with stirring. The reaction mixture was allowed to warm to 25° over 30 minutes and then concentrated in vacuo to remove the acetone. Water (50 ml) was added and the product was extracted with ether. The ether phase was extracted with 1.0N sodium hydroxide, the aqueous layer was separated, acidified and extracted with ether. The dried (over sodium sulfate) extract was concentrated in vacuo to a solid which was crystallized twice from ether-hexane to give 0.63 g, mp 115-116°, (40% yield) of 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hexynoic acid, the titled compound.

Workup

  1. temperatureto warm to 25° over 30 minutes
  2. concentrationconcentrated in vacuo
  3. customto remove the acetone
  4. additionWater (50 ml) was added
  5. extractionthe product was extracted with ether
  6. extractionThe ether phase was extracted with 1.0N sodium hydroxide
  7. customthe aqueous layer was separated
  8. extractionextracted with ether
  9. dry with materialThe dried (over sodium sulfate)
  10. extractionextract
  11. concentrationwas concentrated in vacuo to a solid which
  12. customwas crystallized twice from ether-hexane

Sources & evidence

ORD record
ord-529751be058a46e2bbda978c1aba4d7e
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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