Hydrochloric Acid → 4-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochloride

Reaction equation

[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:19]>>[ClH:19].[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 18617411Methyl 4-(2-Pyrrolidinylethyloxy)benzoate

Product 1

HCID 131748684-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochlorideYield 96%

Procedure

Methyl 4-[2-(1-pyrrolidinyl)ethoxy]benzoate (5.3 g, 21.2 mol) in 1 N aqueous HCl (50 mL) was heated at reflux for 18 h. The reaction mixture was washed with ethyl acetate (2×20 mL). The aqueous solvent was removed under reduced pressure to give the desired acid as a white solid (5.55 g, 96%) after drying under vacuum at ambient temperature.

Workup

temperatureat reflux for 18 h
washThe reaction mixture was washed with ethyl acetate (2×20 mL)
customThe aqueous solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-56d3a7cb790545a484f2d3a938bf450b
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541499B1

Reaction notes

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