Tetrahydrofuran → HCID 58612915, compound
Reaction equation
[CH2:1]([O:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[C:26]([OH:28])=[O:27])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O1CC[CH2:31][CH2:30]1>>[CH2:1]([O:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[C:26]([O:28][CH2:30][CH3:31])=[O:27])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
Procedure
A mixture of 1,2-cyclohexanedicarboxylic acid monohexadecyl ester (white solid m.p.=54-55° C.) (8 g) (prepared from 1,2-cyclohexanedicarboxylic anhydride (1 eq), hexadecanol (1 eq), triethylamine (1 eq), in ethyl acetate at room temperature for 24 hours) in 50 ml of tetrahydrofuran was treated with oxalyl choloride (5 g) overnight at room temperature. After solvent removal in vacuuo the resultant acid chloride was dissolved in 50 ml of absolute ethanol, and sodium carbonate (2.2 g) was added. The mixture was stirred for 3 hours, filtered and concentrated in vacuuo. The light yellow liquid product was dissolved in hexane and passed through a pad of silica gel. Solvent removal gave cyclohexane-1,2-dicarboxylic acid monoethyl ester monohexadecyl ester (5.3 g) as a clear colorless liquid which forms a waxy solid when cooled to below room temperature.
Workup
- additionwas treated with oxalyl choloride (5 g) overnight at room temperature
- customAfter solvent removal in vacuuo the resultant acid chloride
- dissolutionwas dissolved in 50 ml of absolute ethanol
- additionsodium carbonate (2.2 g) was added
- filtrationfiltered
- concentrationconcentrated in vacuuo
- dissolutionThe light yellow liquid product was dissolved in hexane
- customSolvent removal
Sources & evidence
- ORD record
- ord-4832937f74da4fad9f3613c487994982
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07252865B2
Reaction notes
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