Hydrochloric Acid → 2,5,8,11,14,17,20,23,26,29-Decaoxahentriacontan-31-ol
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
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 (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%).
Workup
- customwere removed (0.48 Torr
- customup to 185° C.
- additionThe residual dark oil was diluted with toluene (250 ml)
- additiontreated with calcium chloride (38.1 g)
- stirringAfter stirring for 18 h
- filtrationthe mixture was filtered through Celite
- concentrationconcentrated to a dark oil (102 g), which
- distillationwas fractionally distilled
Sources & evidence
- ORD record
- ord-b9a19cf12b1640d087f83aceb77af307
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07002012B2
Reaction notes
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