Glycolic Acid → HCID 20274488, compound

HRID 371174Notes

Reaction equation

HRID 371174 reaction equation
[CH2:1]([NH2:14])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][NH2:13].[C:15]([OH:19])(=O)[CH2:16][OH:17]>O>[OH:19][CH2:15][C:16]([NH:13][CH2:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][CH2:1][NH:14][C:15](=[O:19])[CH2:16][OH:17])=[O:17]

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 817291-Propanamine, 3,3'-[1,4-butanediylbis(oxy)]bis-

Product 1

HCID 20274488HCID 20274488, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,9-Dioxadodecane-1,12-diamine (22.8 g, 0.112 mole) was placed in a 250 ml round bottom flask and glycolic acid (17.0 g, 0.224 mole) added portion-wise with stirring and cooling. The resultant liquid was heated in an oil bath to 185° C. whereupon distillation of water occurred. Heating was continued at 185° to 195° C. for 2 hours after which time distillation of water subsided and the liquid was poured into a crystallization dish. The resultant oil slowly crystallized in the form of large white clusters; yield 35.5 g (99.3%); m.p. 67°-71° C. The solid was recrystallized from cold absolute methanol to give a white, crystalline product; m.p. 74°-77° C.; infrared (Nujol), 1120 cm-1, 1625 cm-1, 3250 cm-1 ; proton nuclear magnetic resonance (CDCl3 /TMS, 100 MHz), δ1.55-1.95 (complex multiplet, 8 protons), δ3.30-3.65 (complex multiplet, 12 protons), δ4.03 (singlet, 4 protons), δ4.98 (broad singlet, 2 protons), δ7.51 (broad triplet, 2 protons).

Workup

  1. temperaturecooling
  2. temperatureHeating
  3. distillationafter which time distillation of water
  4. additionthe liquid was poured into a crystallization dish
  5. customThe resultant oil slowly crystallized in the form of large white clusters
  6. customThe solid was recrystallized from cold absolute methanol
  7. customto give a white, crystalline product

Sources & evidence

ORD record
ord-650971e018ac4bbf914c13b9409a33e0
Source dataset
uspto-grants-1985_07
Patent number
US04529792

Reaction notes

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