Ethylene Glycol → 6-[4-(2-Hydroxyethoxycarbonylamino)-phenoxy]-hexanoic acid methyl ester

HRID 2169721Notes

Reaction equation

HRID 2169721 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1.[CH2:20]([OH:23])[CH2:21][OH:22]>O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([O:22][CH2:21][CH2:20][OH:23])=[O:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 497644906-(4-Isocyanatophenoxy)-hexanoic acid methyl ester

Product 1

HCID 497644926-[4-(2-Hydroxyethoxycarbonylamino)-phenoxy]-hexanoic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(4-Isocyanato-phenoxy)-hexanoic acid methyl ester 36 (15 g, 57 mmol) was added to ethylene glycol (50 ml) at room temperature. The reaction was exothermic and the temperature rose to 46° C. The reaction mixture was allowed to cool to room temperature and later stirred at room temperature for 16 hours. Water (150 ml) was added and crude 37 was filtered, dried and recrystallised from toluene to get pure 37 (12 g, 84%) as a white powder. M.p: 69.5-71.5° C.

Workup

  1. customrose to 46° C
  2. filtrationcrude 37 was filtered
  3. customdried
  4. customrecrystallised from toluene

Sources & evidence

ORD record
ord-1cc650204ecc40ff8609ffb1cdde3d72
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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