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

HRID 1033142Notes

Reaction equation

HRID 1033142 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>O.CN(C)C=O>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 145735486-(Decyloxy)naphthalen-2-OL

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Decyl monobromide (7.0 g), 2,6-dihydroxynaphthalene (5.0 g) and anhydrous potassium carbonate (4.0 g) were added to 100 ml of dimethylformamide. After stirring at 130° C. for 2 hours, the reaction solution was poured into water. Dilute hydrochloric acid was added to neutralize the solution, which was extracted with diethyl ether. The extract was distilled to remove the solvent to obtain the titled compound as residue (8.0 g).

Workup

  1. extractionwas extracted with diethyl ether
  2. distillationThe extract was distilled
  3. customto remove the solvent

Sources & evidence

ORD record
ord-1366562e8714447b83ddf1f9ea2720fe
Source dataset
uspto-grants-1994_05
Patent number
US05310500

Reaction notes

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