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
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%).
Workup
- customwere removed (64 Pa (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-ddecdbd18791432fbc980e552acef82f
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355646B1
Reaction notes
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