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

HRID 1098711Notes

Reaction equation

HRID 1098711 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-c48c6ac8fc39483fb820f588f0d8a597
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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