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

HRID 1112709Notes

Reaction equation

HRID 1112709 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 1280) 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 cm-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-b1a85b4613224251aa38fc1475d6d103
Source dataset
uspto-grants-1978_10
Patent number
US04123456

Reaction notes

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