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

HRID 83791Notes

Reaction equation

HRID 83791 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-Isocyanatophenoxy)-hexanoic acid methyl ester 18 (15 g, 57 mmol) was added to ethylene glycol (50 ml) at room temp. The reaction was exothermic and the temp. rose to 46° C. Stirring at room temp. for 16 h. was followed by addition of water (150 ml), after which crude 19 was filtered, dried and recrystallised from toluene to get pure 19 (12 g, 84%) as a white powder with an m.p. between 69.5-71.5° C.

Workup

  1. customrose to 46° C
  2. filtrationafter which crude 19 was filtered
  3. customdried
  4. customrecrystallised from toluene

Sources & evidence

ORD record
ord-9b1f4681c4a84f25960ca9893bd0b779
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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