Hydrochloric Acid → HCID 14219918, compound

HRID 732638Notes

Reaction equation

HRID 732638 reaction equation
[OH-].[Li+].[C:3]1([CH2:14][C:15]([O:17]C)=[O:16])[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.C1COCC1.Cl>O.CO>[CH3:13][O:12][C:10](=[O:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 5207741,4-Benzenediacetic acid, dimethyl ester

Product 1

HCID 14219918HCID 14219918, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 655 mg portion of lithium hydroxide was dissolved in 32 ml of water and added to 32 ml of a mixture of 6.4 g of dimethyl 2,2′-(1,4-phenylene)diacetate, 32 ml of THF and 32 ml of methanol. After 2Hours of stirring at room temperature, the reaction solution was neutralized with 1 M hydrochloric acid and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 2.6 g of [4-(2-methoxy-2-oxoethyl)phenyl]acetic acid. EN: 207.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-577ab9811c1b4effad8babaf6bcfbaed
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

Loading…