Water → 2,6-Diisopropylphenol hydrogen adipate

HRID 1383258Notes

Reaction equation

HRID 1383258 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:9]=1[OH:10])[CH3:3].[C:14](Cl)(=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20].[OH2:24]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:14]([OH:22])(=[O:24])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:10][C:9]1[C:4]([CH:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=[CH:7][C:8]=1[CH:11]([CH3:13])[CH3:12])=[O:20]

Participants

6

Reactant 3

HCID 962WaterHCID 4943Propofol2×HCID 61034Adipoyl chloride

Product 1

HCID 226247032,6-Diisopropylphenol hydrogen adipateYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Synthesis of propofol hemiadipate 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

  1. customto reach room temperature
  2. stirringthe two-phase mixture was stirred for 1 hr
  3. washThe organic phase was washed with 3% aqueous HCl
  4. customdried
  5. customSolvents were removed under vacuum
  6. additionThe fractions containing the ester
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-e22b4b8e6d694a8ebfecbf2afe969cc3
Source dataset
uspto-grants-2001_07
Patent number
US06254853B1

Reaction notes

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