Sodium Iodide → 3-(2-Naphthalenylmethoxy)-α-pentylbenzenemethanol

HRID 868434Notes

Reaction equation

HRID 868434 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[OH:13][CH:14]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[OH:13][CH:14]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 117900843-(1-Hydroxyhexyl)phenol

Product 1

HCID 212884963-(2-Naphthalenylmethoxy)-α-pentylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2-bromomethyl naphthalene (5 g, 0.023 mol), 3-(1-hydroxyhexyl)phenol (5 g, 0.026 mol), powdered potassium carbonate (4.5 g, 0.033 mol), sodium iodide (0.4 g, 0.0023 mol) and cesium carbonate (0.7 g, 0.0021 mol) in dry acetone (75 ml) was refluxed overnight (14 hours). The reaction mixture was filtered, the filtrate was concentrated, dissolved in ether, and then washed successively with 1N NaOH solution 6N HCl solution, water and brine. After drying the organics over anhydrous MgSO4, all volatiles were removed. The crude product (5 g) was further purified by chromatography, using 8% ethylacetate in hexanes on silica gel, to yield 3.5 g of the pure desined compound as a colorless liquid.

Workup

  1. temperaturewas refluxed overnight (14 hours)
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutiondissolved in ether
  5. washwashed successively with 1N NaOH solution 6N HCl solution, water and brine
  6. dry with materialAfter drying the organics over anhydrous MgSO4
  7. customall volatiles were removed
  8. customThe crude product (5 g) was further purified by chromatography
  9. customto yield 3.5 g of the

Sources & evidence

ORD record
ord-940045f476264268b22b274eab05092b
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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