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

HRID 638726Notes

Reaction equation

HRID 638726 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-1e179580f93f4bfaad3d7c1bc13ceb43
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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