Reaction equation
C(N(CC)CC)C.[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:12]=1[OH:20])([CH3:10])[CH3:9].[C:21](Cl)(=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27].[OH2:31]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:21]([OH:29])(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:20][C:12]1[C:11]([CH:8]([CH3:10])[CH3:9])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:17]([CH3:19])[CH3:18])=[O:27]Participants
Procedure
Triethylamine (6.26 ml, 45 mmol) and 4-dimethylaminopyridine (50 mg, 0.4 mmol) in methylene chloride (30 ml) were added to a solution of 2,6-diisopropylphenol (5.2 ml, 28 mmol) and adipoyl chloride (4.4 ml, 30 mmol) in methylene chloride (50) at 0° C. The mixture was allowed to reach room temperature and stirred at that temperature for 2 hr. Water (50 ml) was added, and the two-phase mixture was stirred for 1 hr. The organic phase was washed with 3% aqueous HCl and then dried. Solvents were removed under vacuum, and the oily residue was chromatogrammed on a silica gel column using chloroform-methanol (10:0.1) and then chloroform-methanol-acetic acid (10:0.1:0.01). The fractions containing the ester were pooled and evaporated under vacuum to yield 3.4 g (40% yield) of 2,6-diisopropylphenol hydrogen adipate (propofol hemiadipate) as an oil.
Workup
- customto reach room temperature
- stirringthe two-phase mixture was stirred for 1 hr
- washThe organic phase was washed with 3% aqueous HCl
- customdried
- customSolvents were removed under vacuum
- additionThe fractions containing the ester
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-07b7cfb4bcc44c08bad3eb8bc66b7f3b
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362234B1
Linked notes
Loading…