Sodium Hydroxide → HCID 13882821, compound

HRID 978769Notes

Reaction equation

HRID 978769 reaction equation
[S:1]1[C:5]([CH2:6][CH:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]([O:19]CC)=[O:18])[CH:11]=[CH:10][C:9]=3[CH2:8]2)=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>CO>[S:1]1[C:5]([CH2:6][CH:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=[CH:10][C:9]=3[CH2:8]2)=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21289516HCID 21289516, compound

Product 1

HCID 13882821HCID 13882821, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.92 g of ethyl 6-(5-thiazolylmethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was added to a mixture of 10 ml of a 10 % aqueous solution of sodium hydroxide and 30 ml of methanol and the mixture was heated under reflux for 1 hour. The reaction mixture was concentrated to dryness in vacuo and the residue was dissolved in water. A small amount of insoluble material was removed by filtration and the filtrate was adjusted to pH 6 with hydrochloric acid. The precipitate formed was collected by filtration to give 2.71 g of 6-(5thiazolylmethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid as a powder. The powder was suspended in 20 ml of water and 0.42 g of sodium hydroxide was added thereto. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo. The residue was recrystallized from a mixture of ethanol and diethyl ether to give 1.92 g of sodium carboxylate of the above product as a colorless powder with m.p. above 280° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated to dryness in vacuo
  4. dissolutionthe residue was dissolved in water
  5. customA small amount of insoluble material was removed by filtration
  6. customThe precipitate formed
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-92353bb0a5124b76a571e59df9d24410
Source dataset
uspto-grants-1987_05
Patent number
US04665188

Reaction notes

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