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Hydrochloric Acid → Ethyl 4-benzyloxyphenyl-2,4-dioxobutanoate

HRID 322930
Notes
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Reaction equation

HRID 322930 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-:11]CC.[K+].[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)=O.Cl>CCOCC>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH:16]([CH:15]=[O:11])[C:2](=[O:4])[C:1]([O:8][CH2:9][CH3:10])=[O:7])=[CH:19][CH:20]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneHCID 23670592Potassium ethoxide

Product 1

HCID 86756594Ethyl 4-benzyloxyphenyl-2,4-dioxobutanoateYield 97.1%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Conditions

Temperature
0 °C

Procedure

Diethyl oxalate (17.7 g) is added in one portion to a stirred suspension of potassium ethoxide (10.2 g) in anhydrous ether (1000 mL). The stirred mixture is cooled to 0° C., treated with 4-benzyloxyacetophenone (25 g) portionwise, and stirring continued for 3 hours. After standing at room temperature for 18 hours the reaction mixture is poured onto 1 N hydrochloric acid (500 mL) and the organic phase separated. The organic phase is washed with water, dried over magnesium sulphate and evaporated to give ethyl 4-benzyloxypheyl-2,4-dioxobutanoate (35 g).

Workup

  1. waitAfter standing at room temperature for 18 hours
  2. customthe organic phase separated
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-ac3842eed7fe49118cd750bc229b0c1c
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211234B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes