Hydrochloric Acid → HCID 19421582, compound

HRID 744102Notes

Reaction equation

HRID 744102 reaction equation
[OH-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1/[C:13](/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14]\[C:15]([O:17]CC)=[O:16].O.Cl>C(O)C.O1CCCC1>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1/[C:13](/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14]\[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86746610HCID 86746610, compound

Product 1

HCID 19421582HCID 19421582, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

24 ml of a 10% w/v aqueous solution of sodium hydroxide were added to a solution of 2.411 g of ethyl (Z)-3-(2-naphthyl)-3-phenylacrylate (prepared as described in Preparation 112) in 48 ml of ethanol and 24 ml of tetrahydrofuran. The mixture was stirred for 15 hours at room temperature and then poured into water. The pH of the resulting mixture was adjusted to a value of 2 by the addition of concentrated hydrochloric acid, and the mixture was then extracted twice with methylene chloride. The combined extracts were washed with water and dried over anhydrous sodium sulfate; the solvent was then removed by evaporation under reduced pressure. The residue was recrystallized from a mixture of methylene chloride and hexane, to give 2.005 g of the title copound, melting at 170°-172° C.

Workup

  1. extractionthe mixture was then extracted twice with methylene chloride
  2. washThe combined extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was then removed by evaporation under reduced pressure
  5. customThe residue was recrystallized from a mixture of methylene chloride and hexane
  6. customto give 2.005 g of the title copound, melting at 170°-172° C.

Sources & evidence

ORD record
ord-82fb7e5b4f074bf3ac48c43376d4a2f1
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

Loading…