Propofol → 6-(4-Hydroxy-3,5-diisopropyl-phenyl)-6-oxo-hexanoic acid ethyl ester

HRID 2289679Notes

Reaction equation

HRID 2289679 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=O.[C:12](Cl)(=O)C(Cl)=O.[CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:22]=1[OH:30])([CH3:20])[CH3:19].[Cl-].[Al+3].[Cl-].[Cl-]>O1CCCC1.ClCCCl>[CH2:11]([O:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:25]1[CH:26]=[C:21]([CH:18]([CH3:20])[CH3:19])[C:22]([OH:30])=[C:23]([CH:27]([CH3:29])[CH3:28])[CH:24]=1)=[O:8])[CH3:12]

Participants

7

Reactant 4

HCID 4943PropofolHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 6994472Methyl adipate

Product 1

HCID 537233496-(4-Hydroxy-3,5-diisopropyl-phenyl)-6-oxo-hexanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Monomethyl adipate (61 g, 350 mmol) was treated with excess oxalyl chloride in tetrahydrofuran. The mixture was concentrated, and the resulting acid chloride was mixed with 2,6-Diisopropyl phenol (57 g, 350 mmol) at 0° C. Aluminum chloride (93 g, 700 mmol) and a catalytic amount of 1,2-dichloroethane were added in portions, and the mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with 1 M HCl and extracted with ethyl acetate. Concentrated in vacuo and chromatographed the residue to give the expected product.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe reaction was quenched with 1 M HCl
  3. extractionextracted with ethyl acetate
  4. concentrationConcentrated in vacuo
  5. customchromatographed the residue

Sources & evidence

ORD record
ord-86e580c554e046179e9c0f8d2a9ae1ca
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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