Solketal → 3-[(12-Cyclohexyldodecyl)oxy]propane-1,2-diol
Reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1(C)[O:25][CH:24]([CH2:26][OH:27])[CH2:23][O:22]1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.CCCCCC>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:22][CH2:23][CH:24]([OH:25])[CH2:26][OH:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 40.8 g (0.123 mole) of 12-cyclohexyldodecyl bromide, 22.7 g (0.172 mole) of 1,2-isopropylideneglycerol, 1.0 g of cetyltrimethylammonium chloride and 27.6 g (0.344 mole) of 50% aqueous sodium hydroxide solution was stirred at 80° C. for 10 hours. To the reaction mixture was added 200 ml of hexane and the resulting mixture was washed with water, dried (MgSO4) and concentrated under reduced pressure. To the residue were added 200 ml of methanol and 4 ml of 6N hydrochloric acid, and the mixture was heated unde reflux for 10 hours. The mixture was cooled and the colorless crystals precipitated were collected by filtration, washed with hexane and dried to give 10.1 g of the above-mentioned compound. The mother liquid was further cooled to obtain 20.8 g of the second crystals. Total yield: 30.9 g (yield: 74%)
Workup
- washthe resulting mixture was washed with water
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- additionTo the residue were added 200 ml of methanol and 4 ml of 6N hydrochloric acid
- temperaturethe mixture was heated unde
- temperaturereflux for 10 hours
- temperatureThe mixture was cooled
- customthe colorless crystals precipitated
- filtrationwere collected by filtration
- washwashed with hexane
- customdried
Sources & evidence
- ORD record
- ord-c4e48e577029406585e36a21982318c6
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04778912
Reaction notes
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