Lithium hydroxide, monohydrate → 3-((2-(2-Hydroxyethoxy)ethyl)carbamoyl)benzoic acid

HRID 926880Notes

Reaction equation

HRID 926880 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15]C)=[O:14])=[O:9].O.[OH-].[Li+]>O1CCCC1.O>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([OH:15])=[O:14])=[O:9]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66586899Methyl 3-((2-(2-hydroxyethoxy)ethyl)carbamoyl)benzoate

Product 1

HCID 665867923-((2-(2-Hydroxyethoxy)ethyl)carbamoyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 500-mL round bottom flask, was placed a solution of methyl 3-((2-(2-hydroxyethoxyl)ethyl)carbamoyl)benzoate (10 g, 37.45 mmol, 1.00 equiv) in tetrahydrofuran (40 mL), and a solution of lithium hydroxide hydrate (23.4 g, 558.33 mmol, 15.00 equiv) in water (30 mL). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The solution was adjusted to pH 3-4 with hydrochloric acid (2 mol/L), extracted with 3×10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×10 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane:methanol (50:1). This resulted in 5 g (53%) of 3-((2-(2-hydroxyethoxyl)ethyl)carbamoyl)benzoic acid as a yellowish solid. 1H-NMR (300 MHz, DMSO, ppm): δ 13.25(s, 1H), 8.71(m, 1H), 8.48(d, J=8.5 Hz 1H), 8.06(m, 2H), 7.62(m, 1H), 4.59(s, 1H), 3.41-3.60 (m, 8H). MS (ES, m/z): 254 [M+H]+.

Workup

  1. customInto a 500-mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. extractionextracted with 3×10 mL of ethyl acetate
  4. washThe resulting mixture was washed with 2×10 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. washeluted with dichloromethane:methanol (50:1)
  8. customThis resulted in 5 g (53%) of 3-((2-(2-hydroxyethoxyl)ethyl)carbamoyl)benzoic acid as a yellowish solid

Sources & evidence

ORD record
ord-508cc9904fc84b21b96dde3db8ca2506
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

Loading…