Acetone → 9-(3-Hydroxy-5-oxocyclopent-1-EN-1-YL)nonanoic acid

HRID 261910Notes

Reaction equation

HRID 261910 reaction equation
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:3]1.CC(C)=[O:21].O.[K+].[Br-]>[B-](F)(F)(F)F.[Ag+].CO>[OH:21][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:3]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 253877Potassium BromideHCID 204656274-Bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one

Product 1

HCID 132897909-(3-Hydroxy-5-oxocyclopent-1-EN-1-YL)nonanoic acid

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 57.2 g. of crude 4-bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one (Example 13) in 500 ml. of acetone and 325 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during a 15-minute period. The mixture is stirred at 0°-3° C. for 2 hours and filtered. The filtrate is diluted with water, saturated with solid sodium chloride, and extracted with ether. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Partition chromatography of the residue on Celite gives white crystals, m.p. 58°-66° C., λmax.MeOH =223 mμ (7800); νmax (KBr)=3340 (hydroxyl groups), 1705 (carbonyl groups), and 1625-1 (olefin group).

Workup

  1. filtrationfiltered
  2. additionThe filtrate is diluted with water, saturated with solid sodium chloride
  3. extractionextracted with ether
  4. washThe extract is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customPartition chromatography of the residue on Celite
  8. customgives white crystals, m.p. 58°-66° C., λmax

Sources & evidence

ORD record
ord-9d224c9bb58b4880a9108ed35f39d59a
Source dataset
uspto-grants-1979_05
Patent number
US04152524

Reaction notes

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