Sodium hydride → 1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane

HRID 276803Notes

Reaction equation

HRID 276803 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[CH3:49][O:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonateHCID 11164646Hexaethylene Glycol Monobenzyl Ether

Product 1

HCID 114778901-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontaneYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of hexaethylene glycol monobenzyl ether from above (22.3 g) in anhydrous THF (100 ml) was added to a suspension of 50% NaH (3.5 g) in anhydrous THF (100 ml). The suspension was stirred at ambient temperature for 30 min and then a solution of triethylene glycol methyl tosyl ether from above (22.0 g) in THF (100 ml) was added dropwise. The mixture was refluxed under nitrogen overnight, cooled to ambient temperature, quenched with water (500 ml), and extracted with diethyl ether (3×300 ml). The ether extracts were combined, dried (sodium sulfate), and concentrated in vacuo to give nonaethylene glycol benzyl methyl ether as an oil (27 g, 88%), 1H-NMR (CDCl3) δ: 7.31 (m, 5, 5 phenyl CH), 4.54 (s, 2, benzyl CH2), 3.62-3.52 (m, 36, 18 CH2O), 3.35 (s, 3, CH3).

Workup

  1. temperatureThe mixture was refluxed under nitrogen overnight
  2. temperaturecooled to ambient temperature
  3. customquenched with water (500 ml)
  4. extractionextracted with diethyl ether (3×300 ml)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2f17f36ea7642cc97e5cca13ff6d85c
Source dataset
uspto-grants-2002_03
Patent number
US06355646B1

Reaction notes

Loading…