3-Hydroxybenzyl alcohol → Aspirin

HRID 2122061Notes

Reaction equation

HRID 2122061 reaction equation
[OH:1]CC1C=C(O)C=CC=1.C(N(CC)CC)C.[C:17]([O:20][C:21]1[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:23](Cl)=[O:24])(=[O:19])[CH3:18]>C1(C)C=CC=CC=1.O>[C:17]([O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:1])=[O:24])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 2244AspirinYield 200%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

3-hydroxymethylphenol (10 g, 0.08 moles) is dissolved in toluene (50 ml) containing triethylamine (9.8 g, 0.1 moles). To the so obtained solution an acetylsalicylic acid chloride solution (16 g, 0.08 moles) in toluene (50 ml) is added at a temperature of 5°-10° C. under stirring. The mixture is maintained at a temperature in the above mentioned range, under stirring for 2 hours, then poured in water and then extracted with dichloromethane (2×100 ml). The organic phase is separated, washed in sequence with a 25% w/v potassium carbonate solution, with water, with a 3% hydrochloric acid solution and lastly with water again, then anhydrified with sodium sulphate and the solvent evaporated under vacuum. The residue is crystallized from isopropanol. 3-hydroxymethylphenyl ester of the 2-acetoxybenzoic acid (45.8 g, 0.16 moles, yield 80%) is obtained.

Workup

  1. temperatureThe mixture is maintained at a temperature in the
  2. stirringunder stirring for 2 hours
  3. extractionextracted with dichloromethane (2×100 ml)
  4. customThe organic phase is separated
  5. washwashed in sequence with a 25% w/v potassium carbonate solution, with water, with a 3% hydrochloric acid solution and lastly with water again
  6. customthe solvent evaporated under vacuum
  7. customThe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-8506c41f362147718d0510ce369ea929
Source dataset
uspto-grants-2004_02
Patent number
US06696591B1

Reaction notes

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