Hydrochloric Acid → HCID 10466391, compound

HRID 893149Notes

Reaction equation

HRID 893149 reaction equation
C([O:8][CH2:9][C@@H:10]([CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])C1C=CC=CC=1.C1CCCCC=1.Cl>C1COCC1.[C].[Pd]>[OH:8][CH2:9][C@@H:10]([CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 14523998HCID 14523998, compound

Product 1

HCID 10466391HCID 10466391, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(2R)-3-benzyloxy-2-(1-naphthylmethyl)propionic acid was dissolved in 6 ml of THF, and 3 ml of cyclohexene, 2.5 ml of 1N hydrochloric acid and 400 mg of 10% palladium carbon were added thereto. The mixture was refluxed under heating for 48 hours. After filtration, the solvent was distilled off under reduced pressure, and the residue was divided with ethyl acetate and a 4% sodium hydrogencarbonate aqueous solution. The aqueous layer was adjusted to pH2 with 1N hydrochloric acid under cooling with ice and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and a saturated sodium chloride aqueous solution and dried over anhydride sodium sulfate to obtain 212 mg of (2R)-3-hydroxy-2-(1-naphthylmethyl)propionic acid as colorless oily substance.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 48 hours
  3. filtrationAfter filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. temperatureunder cooling with ice
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed sequentially with water
  8. dry with materiala saturated sodium chloride aqueous solution and dried over anhydride sodium sulfate

Sources & evidence

ORD record
ord-10fedad07a58457689aceaf5a40e8d7c
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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