Sodium Hydroxide → HCID 68840681, compound

HRID 1889286Notes

Reaction equation

HRID 1889286 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:15]=[CH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:19]1([CH2:18][CH2:17][CH:16]=[CH:15][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:5]=2[C:3]([OH:4])=[O:2])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68846043HCID 68846043, compound

Product 1

HCID 68840681HCID 68840681, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

175 mg 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid methyl ester were reacted with 1 ml of 2 M aqueous sodium hydroxide in 1.5 ml methanol and 4 ml THF for 1 h at 60° C. The organic solvents were removed in vacuo, the mixture was acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated to yield 165 mg of a mixture of the (E)- and (Z)-isomers of 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid.

Workup

  1. customThe organic solvents were removed in vacuo
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d063c6d515f146bfbe2d47adb795fed2
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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