2,3-Dihydroxynaphthalene → HCID 19004539, compound

HRID 2225716Notes

Reaction equation

HRID 2225716 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.O>[O:21]([CH2:20][CH2:19][O:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 70912,3-DihydroxynaphthaleneHCID 68526Benzene, (2-bromoethoxy)-HCID 516892Sodium Bicarbonate

Product 1

HCID 19004539HCID 19004539, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2,3-dihydroxynaphthalene (5.6 g) and sodium bicarbonate powder (2.9 g) in dimethylformamide (50 mL) was stirred and heated at 135° C. for 1 hour. When the gas evolution ceased, the mixture was cooled to about 60° C. and beta-bromophenetole (7 g) was added. The mixture was stirred at 60° C. overnight, cooled, diluted with water and filtered. The solids were crystallized from dichloromethane-diethyl ether to give 3.9 g of 3-(2-phenoxyethoxy)-2-naphthol as a colorless solid, mp 141°-142° C.

Workup

  1. temperaturethe mixture was cooled to about 60° C.
  2. stirringThe mixture was stirred at 60° C. overnight
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe solids were crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-f0f6e6e5113343659179d97b04ce64c9
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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