Butyl Chloride → HCID 118516619, compound
Reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([O-:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[Na+].[CH2:26](Cl)[CH2:27][CH2:28][CH3:29]>C1COCC1>[CH2:26]([O:24][CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:27][CH2:28][CH3:29]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 fahrenheit
Procedure
40.3 g (0.118 mole) 12-tricosanol (Example 2) was heated with 3.0 g (0.13 mole, 10% molar excess) sodium metal to 130° C. for a period of 15 hrs during which most of the sodium dissolved with hydrogen evolution to form the corresponding alkoxide, sodium 12-tricosanolate, which is liquid at 130° C. The thus prepared sodium 12-tricosanolate was subsequently treated with 20 ml (0.19 mole, 60% molar excess) n-butyl chloride in the presence of 20 ml THF at 90° C. for 7 days. The resulting reaction mixture was quenched with aqueous sodium hydroxide and extracted with heptane. The heptane solution was cooled to 20° F. during which 8.9 g of solid precipitate (unconverted 12-tricosanol and 12-tricosanone) formed and was removed. The heptane was evaporated at 80° C., 10 torr to yield the 12-tricosanyl n-butyl ether (33.2 g) as a colorless oil having the following properties: VI=147, VIS100=2.768 cSt, VIS40=9.395, cloud point: −3° C., pour point: −4° C.
Workup
- customat 130° C
- customThe resulting reaction mixture
- customwas quenched with aqueous sodium hydroxide
- extractionextracted with heptane
- customformed
- customwas removed
- customThe heptane was evaporated at 80° C.
Sources & evidence
- ORD record
- ord-cd4ab4f0c387497bb5dc18540a53469e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193653B1
Reaction notes
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