Sodium Hydroxide → HCID 67768016, compound

HRID 743468Notes

Reaction equation

HRID 743468 reaction equation
[OH-].[Na+].Cl.C[O:5][C:6](=[O:23])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]=1[Cl:22]>O.CO>[ClH:13].[Cl:22][C:8]1[C:9]([O:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=1[C:6]([OH:23])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70087905HCID 70087905, compound

Product 1

HCID 67768016HCID 67768016, compoundYield 169.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of NaOH (2.73 g, 68.25 mmol) in 80 ml of water and 40 ml of methanol was added in one portion 8 g (22.56 mmol) of 2,6-dichloro-3-(2-pyrrolidinoethoxy)benzoic acid methyl ester hydrochloride and the mixture was heated at 90° C. for 15 hours. The mixture was concentrated in vacuo to remove methanol, the aqueous layer was acidified with 20 ml of conc. HCl solution, and the white solid was filtered. The white solid was dissolved in hot water, filtered, and the filtrate was treated with 15 ml of conc. HCl solution. The solid product was recrystallized from methanol/ether to afford 6.53 g (85%) of 2,6-dichloro-3-(2-pyrrolidinoethoxy)benzoic acid hydrochloride (Formula III: Ar=2,6-Cl2 -3- (OCH2CH2 -1-pyrrolidinyl)phenyl) as a white crystalline solid, m.p. 257°-259° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove methanol
  3. filtrationthe white solid was filtered
  4. dissolutionThe white solid was dissolved in hot water
  5. filtrationfiltered
  6. additionthe filtrate was treated with 15 ml of conc. HCl solution
  7. customThe solid product was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-83f96891b0544d96add837dec35e9f54
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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