Hydrochloric Acid → HCID 67541868, compound

HRID 872014Notes

Reaction equation

HRID 872014 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([O:20]CC)=[O:19])[CH:9]=1.Cl>C(O)C>[CH3:3][O:4][CH2:5][CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]([OH:20])=[O:19])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67543580HCID 67543580, compound

Product 1

HCID 67541868HCID 67541868, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5N Aqueous solution of sodium hydroxide (3.4 ml) was added to a solution of ethyl 4-(3-methoxypropyl)-2-naphthoate (2.41 g) in ethanol and the mixture was stirred at room temperature for 3 hours. The reaction solution was acidified by adding 10% hydrochloric acid under ice-cooling and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The resulted residue was triturated in n-hexane to give 4-(3-methoxypropyl)-2-naphthoic acid (2.09 g) as a colorless powder.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was triturated in n-hexane

Sources & evidence

ORD record
ord-3789fe308ea14d9a8f51e3dc00fbd46e
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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