Glycolic Acid → 4,4'-Methylenebis(hydroxyacetamidocyclohexane)

HRID 371172

Reaction equation

HRID 371172 reaction equation
[CH2:1]([CH:9]1[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]1)[CH:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.[C:16]([OH:20])(=O)[CH2:17][OH:18]>C(O)(C)C.C(O)C>[CH2:1]([CH:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:16](=[O:20])[CH2:17][OH:18])[CH2:6][CH2:7]1)[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:17](=[O:18])[CH2:16][OH:20])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 757Glycolic AcidHCID 156604,4'-Diaminodicyclohexylmethane

Product 1

HCID 542181664,4'-Methylenebis(hydroxyacetamidocyclohexane)

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

4,4'-Methylenebis(cyclohexylamine) (56.5 g, 0.27 mole) was dissolved in hot isopropanol (500 ml) and glycolic acid (40.9 g, 0.54 mole) added portion-wise with stirring. Upon cooling, a white gummy solid separated which was isolated by decantation and redissolved in a small volume of ethanol. Crystallization produced a white crystalline, deliquescent solid; m.p. 96°-102° C. Thorough drying under vacuum increased the melting point (m.p. 149°-151° C.) and reduced the deliquescence.

Workup

  1. temperatureUpon cooling
  2. customa white gummy solid separated which
  3. customwas isolated by decantation
  4. customCrystallization
  5. customproduced a white crystalline, deliquescent solid
  6. customThorough drying under vacuum
  7. temperatureincreased the melting point (m.p. 149°-151° C.)

Sources & evidence

ORD record
ord-c58731c0f88949cf8bb000b49c348c0d
Source dataset
uspto-grants-1985_07
Patent number
US04529792

Linked notes

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