3-Bromo-1-propanol → HCID 22229113, compound

HRID 1744391Notes

Reaction equation

HRID 1744391 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.Br[CH2:14][CH2:15][CH2:16][OH:17].[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:14][CH2:15][CH2:16][OH:17])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 14797Potassium HydroxideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 22229113HCID 22229113, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

mixture of 6-bromo-2-naphthol (10.0 g), 3-bromopropanol (9.4 g) and potassium hydroxide (3.0 g) in 50 ml of ethanol was refluxed for 16 h. The mixture was washed with diethyl ether and water. The combined organic layers were dried, filtered, and concentrated. The crude product was crystallized from ethanol to give 6-bromo-2-(3-hydroxypropyloxy)-naphthalene in 40% yield.

Workup

  1. temperaturewas refluxed for 16 h
  2. washThe mixture was washed with diethyl ether and water
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-93e12c58cba245d896e8ca389a00e987
Source dataset
uspto-grants-2006_03
Patent number
US07015301B2

Reaction notes

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