Acetic Acid → HCID 15434653, compound

HRID 369486Notes

Reaction equation

HRID 369486 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH2:21]1[O:23][CH2:22]1.[C:24](O)(=[O:26])[CH3:25]>O>[OH:26][CH2:24][CH2:25][N:1]([CH2:22][CH2:21][OH:23])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 15434652HCID 15434652, compound

Product 1

HCID 15434653HCID 15434653, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-amino-3-octoxybenzoate (3.47 g, 12.4 mmol) and ethylene oxide (4.5 g, 198 mol) were dissolved in 100 mL acetic acid to form a reaction mixture. The mixture was stirred at room temperature for 12 hours. It was then diluted with H2O (500 mL), extracted with chloroform/methanol (95/5, 4×100 mL). The organic extract was concentrated to brown oil. Flash chromatographic purification (silica gel, 5% to 10% methanol in chloroform) afforded the intermediate methyl 4-bis(2'-hydroxyethyl)amino-3-octoxybenzoate as an off-white oil (2.25 g, 42%). 1H NMR (300 MHz, CDCl3): 7.62 (dd, J=8.1, 2.1 Hz, 1H), 7.55 (d, J=2.1 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 4.06 (t, J=6.9 Hz, 2H), 3.90 (s, 3H), 3.64 (t, J=5.1 Hz, 4H), 3.38 (t, J=5.1 Hz, 4H), 1.86 (J=5.1 Hz, 2H), 1.30 (m, 10H), 0.89 (t, J=6.9 Hz, 3H). ESMS calcd (C20H33NO5): 367.2; found: 390.3 (N+Na)+.

Workup

  1. customto form a reaction mixture
  2. extractionextracted with chloroform/methanol (95/5, 4×100 mL)
  3. extractionThe organic extract
  4. concentrationwas concentrated to brown oil
  5. customFlash chromatographic purification (silica gel, 5% to 10% methanol in chloroform)

Sources & evidence

ORD record
ord-e826d5ca8df14d0491ba78cbe3285262
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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