Hydrochloric Acid → 2,5,8,11,14,17,20,23,26,29-Decaoxahentriacontan-31-ol

HRID 2304823Notes

Reaction equation

HRID 2304823 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([OH:19])[CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[Cl-].C[CH:22]([OH:40])[CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38]O.Cl>>[CH3:1][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:19][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][OH:40]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8200Tetraethylene GlycolHCID 23665647Potassium tert-butoxideHCID 86589670HCID 86589670, compound

Product 1

HCID 145505472,5,8,11,14,17,20,23,26,29-Decaoxahentriacontan-31-olYield 45%

Conditions

Temperature
120 °C

Procedure

Potassium t-butoxide (Aldrich, 95%, 39.0 g) was added to a solution of tetraethylene glycol (Aldrich, 412.7 g) and methyl hexaethylene glycol chloride from above (95.8 g) at 18° C. over a 25 min period (ice/acetone bath). The reaction mixture was then stirred at 120° C. overnight. The pH was adjusted to 7 by the addition of hydrochloric acid (12 N, 11.7 ml), and volatiles were removed (64 Pa (0.48 Torr), up to 185° C.). The residual dark oil was diluted with toluene (250 ml), and treated with calcium chloride (38.1 g). After stirring for 18 h, the mixture was filtered through Celite™ and concentrated to a dark oil (102 g), which was fractionally distilled to provide decaethylene glycol monomethyl ether as an amber oil (64.4 g, 45%). An analytical sample was obtained via chromatography on silica gel, eluting with 4% methanol in chloroform to provide a colorless oil; 1H-NMR (DMSO-d6) δ: 4.58 (t, J=5.5 Hz, 1, OH), 3.58-3.38 (m, 40, 20 OCH2), 3.24 (s, 3, OCH3).

Workup

  1. customwere removed (64 Pa (0.48 Torr)
  2. customup to 185° C.
  3. additionThe residual dark oil was diluted with toluene (250 ml)
  4. additiontreated with calcium chloride (38.1 g)
  5. stirringAfter stirring for 18 h
  6. filtrationthe mixture was filtered through Celite™
  7. concentrationconcentrated to a dark oil (102 g), which
  8. distillationwas fractionally distilled

Sources & evidence

ORD record
ord-504800c92a2c4324a4a0f4e70e007226
Source dataset
uspto-grants-2002_08
Patent number
US06437124B1

Reaction notes

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