Hydrochloric Acid → HCID 67528487, compound

HRID 2261808Notes

Reaction equation

HRID 2261808 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18667930Dimethyl 5-butoxyisophthalate

Product 1

HCID 67528487HCID 67528487, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A suspension of 5-butoxy-isophthalic acid dimethyl ester (2.0 g, 7.5 mmol) in THF/MeOH/water (5.0 mL each) is treated with lithium hydroxide (0.22 g, 9.0 mmol) at room temperature for 1.0 h. The reaction mixture is acidified with 1.0 M HCl and the product is extracted with EtOAc (30 mL), washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as solid (1.0 g, 53%). LC-ES/MS m/e 270.3 (M+18), 251.3 (M−1).

Workup

  1. extractionthe product is extracted with EtOAc (30 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-d0610719a45644cea393d641a792d23f
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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