1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane → Nonaethylene Glycol Monomethyl Ether

HRID 276808Notes

Reaction equation

HRID 276808 reaction equation
C[O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][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][O:26][CH2:27][CH2:28][O:29][CH2:30]C1C=CC=CC=1>C(O)C.[Pd]>[CH3:30][O:29][CH2:28][CH2:27][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][CH2:7][CH2:6][O:5][CH2:4][CH2:3][OH:2]

Participants

4

Reactant 1

HCID 114778901-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane

Product 1

HCID 11339376Nonaethylene Glycol Monomethyl EtherYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of nonaethylene glycol benzyl methyl ether (10 g, 19.3 mmol) in ethanol (200 mL) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen at 344.7 kPa (50 psi) on a Parr apparatus for 3 h. The catalyst was filtered off (Celite™), and the filtrate was concentrated in vacuo and dried by evaporation of toluene to provide nonaethylene glycol monomethyl ether as an oil (8.17 g, 99%), 1H-NMR (DMSO-d6) δ: 4.56 (t, 1 OH), 3.60-3.35 (m, 36, 18 OCH2), 3.22 (s, 3, CH3).

Workup

  1. filtrationThe catalyst was filtered off (Celite™)
  2. concentrationthe filtrate was concentrated in vacuo
  3. dry with materialdried by evaporation of toluene

Sources & evidence

ORD record
ord-7517962ce0e44655aa6976e9c827fa80
Source dataset
uspto-grants-2002_03
Patent number
US06355646B1

Reaction notes

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