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]([CH2:26][OH:27])[OH:25])[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 solution of sodium hydroxide was stirred at 80° C. for 10 hours. Then to the reaction mixture was added 200 ml of hexane, and the resulting mixture was washed with water, and dried (MgSO4), followed by evaporation of the solvent under reduced pressure. To the residue were added 200 ml of methanol and 4 ml of 6N hydrochloric acid, and the mixture was heated under reflux for 10 hours and then cooled. The precipitated colorless crystals were collected by filtration, washed with hexane, and dried, to give 10.1 g of the above-captioned compound. The mother liquid was further cooled, to give 20.8 g of the second crystals. Overall yield: 30.9 g (74%)
Workup
- washthe resulting mixture was washed with water
- dry with materialdried (MgSO4)
- customfollowed by evaporation of the solvent under reduced pressure
- additionTo the residue were added 200 ml of methanol and 4 ml of 6N hydrochloric acid
- temperaturethe mixture was heated
- temperatureunder reflux for 10 hours
- temperaturecooled
- filtrationThe precipitated colorless crystals were collected by filtration
- washwashed with hexane
- customdried
Sources & evidence
- ORD record
- ord-f44569ecebf5436b8d694d2ede416a36
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04889953
Reaction notes
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