Hydrochloric Acid → HCID 54589775, compound

HRID 531422Notes

Reaction equation

HRID 531422 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][N:43]=[N+:44]=[N-:45])[C:21]=1[O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:31]=[N+:32]=[N-:33])[C:16]([O-:18])=[O:17])=[N+:2]=[N-:3].O.Cl>C1COCC1>[N:43]([CH2:42][CH2:41][O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][C:20]1[CH:19]=[C:15]([CH:14]=[C:13]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[C:21]=1[O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:31]=[N+:32]=[N-:33])[C:16]([OH:18])=[O:17])=[N+:44]=[N-:45]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 117702861HCID 117702861, compound

Product 1

HCID 54589775HCID 54589775, compoundYield 136.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in which the 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoate (2.18 g, 3.32 mmol) of Chemical Formula 11 was dissolved in THF, water-soluble LiOH (1 M) (9.96 mL, 9.96 mmol) was added at room temperature, and the mixture was heated under reflux for 4 hours. The post-reaction mixture was cooled to room temperature, and was acidified to pH 4 by adding 0.1 N HCl. This mixture was partitioned to distilled water (40 mL) and ethyl acetate (100 mL), the organic layer was separated, washed with saturated salted water (15 mL), dried with anhydrous sodium sulfate, then filtered, and the resulting filtrate was vacuum distilled to give 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoic acid (2.90 g, 98%). 1H NMR (500 MHz, CDCl3) δ 7.35 (s, 2H), 4.18-4.29 (m, 6H), 3.81-3.88 (m, 6H), 3.73 (m, 6H), 3.65-3.68 (m, 12H), 3.38 (m, 6H); 13C NMR (125 MHz, CDCl3) δ 170.9, 152.4, 143.3, 124.0, 109.6, 72.5, 70.9 (3), 70.8 (3), 70.6, 70.1 (3), 69.8 (2), 68.9 (2), 50.7 (3).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThis mixture was partitioned
  4. distillationto distilled water (40 mL) and ethyl acetate (100 mL)
  5. customthe organic layer was separated
  6. washwashed with saturated salted water (15 mL)
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationdistilled

Sources & evidence

ORD record
ord-d3275569e6424175a4e61dbe9a193566
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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