Lithium Hydroxide → (Z)-3-(2-naphthyl)prop-2-enoic acid

HRID 1934885Notes

Reaction equation

HRID 1934885 reaction equation
C([O:3][C:4](=[O:17])/[CH:5]=[CH:6]\[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)C.[OH-].[Li+]>O1CCCC1.O>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1/[CH:6]=[CH:5]\[C:4]([OH:17])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69822035HCID 69822035, compound

Product 1

HCID 1712266(Z)-3-(2-naphthyl)prop-2-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (Z)-naphthalene-2-acrylic acid ethyl ester (1.38 g, 6.0 mmole) in a mixture of tetrahydrofuran (10 ml) and water (10 ml) was treated with lithium hydroxide (0.88 g, 37 mmol) and heated to 60° C. for 6 hours. On cooling, the organic phase was separated and the. aqueous phase was acidified and extracted with diethyl ether. The ethereal phase was dried and the solvent removed in vaccuo to give (Z)-3-(2-naphthyl)prop-2-enoic acid as a white solid which was used without further purification, Mp 207-209° C.

Workup

  1. temperatureOn cooling
  2. customthe organic phase was separated
  3. extractionextracted with diethyl ether
  4. customThe ethereal phase was dried
  5. customthe solvent removed in vaccuo

Sources & evidence

ORD record
ord-5c83ca8faea3465d9942c2adaa21da38
Source dataset
uspto-grants-2002_05
Patent number
US06384281B1

Reaction notes

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