Water → Aspirin

HRID 558033Notes

Reaction equation

HRID 558033 reaction equation
C(C[O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])(O)=O.C(N([CH2:20][CH3:21])CC)C.[OH2:22]>CC(C)=O>[CH3:21][C:20]([O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]([OH:5])=[O:14])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 9920628Benzoic acid, 2-hydroxy-, carboxymethyl ester

Product 1

HCID 2244Aspirin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-hydroxy-benzoic acid carboxymethyl ester (22.8 grams) and triethylamine (22.6 ml) in acetone (200 ml) was added dichloro linker (10 grams). The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 18 hours. The reaction mixture was poured onto cold water and crude product was extracted into ethyl acetate. It was washed with 5% sodium bicarbonate solution and water, followed by drying over sodium sulphate. The solvent was distilled off and precipitated with diisopropyl alcohol to give 8 grams of pure Aspirin dimer diol as a white powder with a melting point of 99-102° C. The product was characterized by IH NMR (DMSO-d6) δ 4.40 (s, 2H, CH2), 4.90 (s, 2H, CH2), 5.15 (s, 2H, CH2), 7.05 (m, 2H, Ar), 7.62 (t, 1H, Ar), 7.90 (d, 1H, Ar), 10.30 (s, 1H, ArOH).

Workup

  1. additionwas added dichloro linker (10 grams)
  2. temperaturerefluxed for 18 hours
  3. extractionwas extracted into ethyl acetate
  4. washIt was washed with 5% sodium bicarbonate solution and water
  5. dry with materialby drying over sodium sulphate
  6. distillationThe solvent was distilled off
  7. customprecipitated with diisopropyl alcohol

Sources & evidence

ORD record
ord-3e4c1088895f442e8cff68239c58aaaa
Source dataset
uspto-grants-2011_11
Patent number
US08062653B2

Reaction notes

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