Hydrochloric Acid → 6-(Decyloxy)naphthalen-2-ol

HRID 247797

Reaction equation

HRID 247797 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]([OH:23])[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]([OH:23])[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 935522,6-Dihydroxynaphthalene

Product 1

HCID 145735486-(Decyloxy)naphthalen-2-olYield 53.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of decylmonobromide (1.5 g), 2,6-dihydroxynaphthalene (1 g) and anhydrous potassium carbonate (0.8 g) in dimethylformamide (50 ml) was stirred at 130° C. for four hours. The solution was poured in water and was made neutral with dilute aqueous hydrochloric acid solution. To the solution was added diethyl ether in order to effect extraction and the extract was distilled to remove the solvent. The residue was washed with hexane and recrystallized from water/ethanol (1/9) to obtain the titled compound (about 1 g).

Workup

  1. extractionextraction
  2. distillationthe extract was distilled
  3. customto remove the solvent
  4. washThe residue was washed with hexane
  5. customrecrystallized from water/ethanol (1/9)

Sources & evidence

ORD record
ord-3dc937dc4f61493886c7a97501948512
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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