Hydrochloric Acid → 1-Methyl 6-tert.-butyl 2-hydroxy-4-oxoadipate

HRID 249546Notes

Reaction equation

C[C:2]1(C)[O:6][CH:5]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4](=[O:18])[O:3]1.C[O-].[Na+].Cl>C1(C)C=CC=CC=1>[OH:6][CH:5]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C:4]([O:3][CH3:2])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (16.30 g, 60.08 mmol) in toluene (120.0 ml) which had been cooled to 0° C., sodium methoxide (1M in methanol) (60.3 ml) was dropwise added in an argon atmosphere. After stirring the solution at 0° C. for 30 minutes, 1N hydrochloric acid (160.5 ml) was dropwise added and the mixture was stirred for 10 minutes at 0° C. Most of the organic solvent was evaporated off under reduced pressure, and the residual mixture was extracted with ethyl acetate and washed with a saturated saline and a phosphate buffer solution (pH 7.0). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:acetone=2:1) to give pure 1-methyl 6-tert.-butyl 2-hydroxy-4-oxoadipate (13.26 g, 53.85 mmol). Yield, 89.6 %.

Workup

stirringthe mixture was stirred for 10 minutes at 0° C
customMost of the organic solvent was evaporated off under reduced pressure
extractionthe residual mixture was extracted with ethyl acetate
washwashed with a saturated saline
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e0116245eeb74d7a8facf0987e8c26f9
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05214197

Reaction notes

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