Hydrochloric Acid → HCID 59512269, compound

HRID 1158462Notes

Reaction equation

HRID 1158462 reaction equation
COCCC[O:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:9]=1.[OH-].[Na+].Cl>O1CCOCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([OH:21])=[O:6])=[CH:9][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68616204HCID 68616204, compound

Product 1

HCID 59512269HCID 59512269, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-chloro-3-(3-methoxy-propoxy)-benzoic acid 3-methoxy-propyl ester (1.58 g, 4.99 mmol) in aqueous 2N NaOH (3.23 mL, 6.48 mmol) and dioxane (10 mL) is stirred at room temperature for 3.5 hrs. The mixture is acidified by addition of 2N HCl, the volatiles are removed by evaporation and the obtained suspension is filtered. The precipitate is washed with ice-cold water and dried in vacuo to give the title compound as white solid. MS: 243.0 [M−H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 3.93 min. 1H-NMR (DMSO-d6): δ 2.00 (m, 2H), 3.27 (s, 3H), 3.34 (s, br, 1H), 3.53 (m, 2H), 4.19 (m, 2H), 7.5-7.6 (m, 3H) ppm.

Workup

  1. customthe volatiles are removed by evaporation
  2. filtrationthe obtained suspension is filtered
  3. washThe precipitate is washed with ice-cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2de5af095a894984a28f743a94b7ec67
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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