Diethyl Oxalate → Ethyl 4-(4-tert-butylphenyl)-2,4-dioxobutanoate

HRID 1510458Notes

Reaction equation

HRID 1510458 reaction equation
[O-]CC.[Na+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[C:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>C(O)C.C1(C)C=CC=CC=1>[C:15]([C:19]1[CH:20]=[CH:21][C:22]([C:25](=[O:27])[CH2:26][C:6](=[O:8])[C:5]([O:12][CH2:13][CH3:14])=[O:11])=[CH:23][CH:24]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 7268Diethyl OxalateHCID 13669p-tert-ButylacetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 43186901Ethyl 4-(4-tert-butylphenyl)-2,4-dioxobutanoateYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent2×

Procedure

To a cooled solution, <5° C., of sodium ethoxide (4.4 g, 64.6 mmol) in ethanol, diethyl oxalate (7.71 mL, 56.7 mmol) in toluene (150 mL) was added. The reaction mixture was stirred for 30 min, before the addition of 1-(4-tert-butylphenyl)ethanone (56.7 mmol, 10 g) dropwise in toluene (20 mL) (via pressurised dropping funnel). The reaction mixture was stirred overnight to room temperature and then evaporated to low volume. Acetic acid was added and the resultant precipitate was filtered and washed with heptane to obtain ethyl 4-(4-tert-butylphenyl)-2,4-dioxobutanoate (15.68 g, 56.7 mmol).

Workup

  1. customevaporated to low volume
  2. additionAcetic acid was added
  3. filtrationthe resultant precipitate was filtered
  4. washwashed with heptane

Sources & evidence

ORD record
ord-ca4099e830e84ac0aeeb29d3de94afd3
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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