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Potassium Hydroxide → alpha[m-(2-Phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionic acid

HRID 1277784
Notes
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Reaction equation

HRID 1277784 reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:19][CH2:18][CH2:17][O:16]2)[CH:10]=1)([CH3:8])[C:4]([O:6]C)=[O:5].[OH-].[K+]>[Zn].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O>[C:20]1([C:15]2([C:11]3[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([OH:6])=[O:5])[CH:14]=[CH:13][CH:12]=3)[O:19][CH2:18][CH2:17][O:16]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 12819455Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate

Product 1

HCID 12819457alpha[m-(2-Phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionic acid

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24463Copper sulfate pentahydrateCatalyst
HCID 962WaterSolvent2×

Procedure

To 456 mg of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate were added 2.00 g of potassium hydroxide and 10 ml of water. The mixture was heated under reflux with stirring. A mixture of 100 mg of zinc powder and 10 mg of copper sulfate pentahydrate was added three times at 30 minutes' intervals, and the mixture was further heated under reflux for 24 hours with stirring. After cooling, 20 ml of water was added. The insoluble matter was separated by filtration, and washed with 20 ml of water. The filtrate and the washing were combined, and extracted with 10 ml of diethyl ether. The organic layer was adjusted to pH 1 with 3.5 ml of conc. hydrochloric acid, and extracted four times with 20 ml of diethyl ether. The organic layer was washed with 10 ml of water, and concentrated under reduced pressure to afford α[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionic acid as colorless crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. additionwas added three times at 30 minutes' intervals
  4. temperaturethe mixture was further heated
  5. temperatureunder reflux for 24 hours
  6. stirringwith stirring
  7. temperatureAfter cooling
  8. customThe insoluble matter was separated by filtration
  9. washwashed with 20 ml of water
  10. extractionextracted with 10 ml of diethyl ether
  11. extractionextracted four times with 20 ml of diethyl ether
  12. washThe organic layer was washed with 10 ml of water
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c67f64a06354ce3af34da1bd86f7e01
Source dataset
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04278802

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes