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

HRID 1835005Notes

Reaction equation

HRID 1835005 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 (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 (300 MHz, DMSO-d6) δ: 4.56 (t, 1H OH), 3.60-3.35 (m, 36H, 18 OCH2), 3.22 (s, 3H, 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-391159597083443998234e37b081f198
Source dataset
uspto-grants-2004_08
Patent number
US06770267B2

Reaction notes

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