Hydrochloric Acid → 2-(3-Methoxy-phenoxy)-3-oxo-succinic acid diethyl ester

HRID 1804785Notes

Reaction equation

HRID 1804785 reaction equation
[O-]CC.[Na+].[CH2:5]([O:7][C:8](=[O:14])[C:9](OCC)=[O:10])[CH3:6].[CH2:15]([O:17][C:18](=[O:29])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH3:16].Cl>C(OCC)C>[CH2:15]([O:17][C:18](=[O:29])[CH:19]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[C:9](=[O:10])[C:8]([O:7][CH2:5][CH3:6])=[O:14])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 21506379Ethyl 2-(3-methoxyphenoxy)acetate

Product 1

HCID 591526762-(3-Methoxy-phenoxy)-3-oxo-succinic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Sodium ethoxide (32.5 g, 454 mmol) is covered with 1 l of dry diethyl ether. Oxalic acid diethyl ester (55.2 ml, 416 mmol) is added drop wise within 20 min. After 30 min stirring at room temperature, the mixture is heated to reflux. A solution of (3-methoxy-phenoxy)-acetic acid ethyl ester (22) (79.5 g, 378 mmol) in 80 ml of dry diethyl ether is added drop wise within 30 min and the mixture is allowed to reflux for 1 hour. After cooling down to room temperature, the reaction mixture is poured on 2M HCl (400 ml)/ice (400 g) and extracted with diethyl ether. The organic layers are dried over sodium sulfate, filtrated and evaporated.

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling down to room temperature
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layers are dried over sodium sulfate
  6. filtrationfiltrated
  7. customevaporated

Sources & evidence

ORD record
ord-30253a59fe34430986cd4358c6c094de
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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