Hydrochloric Acid → HCID 19421582, compound

HRID 1613320Notes

Reaction equation

HRID 1613320 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, compoundYield 91.7%

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 compound, 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

Sources & evidence

ORD record
ord-a2267017440d4628809b697245d43f0a
Source dataset
uspto-grants-1993_03
Patent number
US05192766

Reaction notes

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