Hydrochloric Acid → 2-Naphthalenecarboxylic acid, 6-(decyloxy)-

HRID 247795

Reaction equation

HRID 247795 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23]([OH:25])=[O:24])[CH:19]=2)[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)C>[CH2:1]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23]([OH:25])=[O:24])[CH:19]=2)[CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 103591672-Naphthalenecarboxylic acid, 6-(decyloxy)-Yield 68.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

After a solution of decylmonobromide (7 g), 2-hydroxy-6-carboxynaphthalene (2 g) and anhydrous potassium carbonate (4 g) in dimethylformamide (100 ml) was stirred at 130° C. for two hours, it was poured in water. Dilute aqueous hydrochloric acid solution was added thereto until the solution was neutral. To the solution was added diethylether in order to effect extraction. The extracted layer was distilled to remove the solvent. The residue was added to a solution of sodium hydroxide (3.3 g) in water (10 ml) and ethanol (50 ml). The mixture was refluxed for about one day. Thereto was added dilute aqueous hydrochloric acid solution until the solution was neutral. The solution was distilled to remove the solvent and concentrated. Solid precipitate was collected and recrystallized from water-ethanol mixture to obtain the titled compound (2.4 g).

Workup

  1. extractionextraction
  2. distillationThe extracted layer was distilled
  3. customto remove the solvent
  4. additionThe residue was added to a solution of sodium hydroxide (3.3 g) in water (10 ml) and ethanol (50 ml)
  5. temperatureThe mixture was refluxed for about one day
  6. additionThereto was added dilute aqueous hydrochloric acid solution until the solution
  7. distillationThe solution was distilled
  8. customto remove the solvent
  9. concentrationconcentrated
  10. customSolid precipitate was collected
  11. customrecrystallized from water-ethanol mixture

Sources & evidence

ORD record
ord-809580bbbd2741c2beaa3b6776424a4d
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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