2-Chloroethyl methyl ether → 10-(2-Methoxyethoxy)-2,5,8,12,15,18-hexaoxanonadecane

HRID 430900Notes

Reaction equation

HRID 430900 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]([OH:22])[CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21].Cl[CH2:24][CH2:25][O:26][CH3:27]>>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]([O:22][CH2:24][CH2:25][O:26][CH3:27])[CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21]

Participants

4

Reactant 3

HCID 123162-Chloroethyl methyl etherHCID 14798Sodium HydroxideHCID 12857528HCID 12857528, compound

Product 1

HCID 1876188510-(2-Methoxyethoxy)-2,5,8,12,15,18-hexaoxanonadecaneYield 85%

Conditions

Temperature
60 °C

Procedure

20.4 g (0.51 mol) of NaOH pellets were added to 100 g (0.34 mol) of 1,3-bis[2-(2-methoxyethoxy)ethoxy]-2-propanol resulting from Step 1. 48.2 g (0.51 mol) of 2-chloroethylmethylether was dropwise added in small portions while stirring at 60° C. After the completion of dropwise addition, the mixture was stirred for about 2 hours and a precipitated salt was filtered off, the filtrate was condensed and purified by a vacuum distillation to give 102 g of 1,3-bis[2-(2-methoxyethoxy)ethoxy]-2-(2-methoxyethoxy)propane (E) (yield: 85%). The distillation temperature was from 155 to 161° C./0.2 mmHg.

Workup

  1. additionAfter the completion of dropwise addition
  2. stirringthe mixture was stirred for about 2 hours
  3. filtrationa precipitated salt was filtered off
  4. customcondensed
  5. distillationpurified by a vacuum distillation

Sources & evidence

ORD record
ord-31af3664bd43479087ff6b8e76be7b0d
Source dataset
uspto-grants-2003_12
Patent number
US06656252B2

Reaction notes

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