3-Hydroxybenzyl alcohol → Aspirin

HRID 2224648Notes

Reaction equation

HRID 2224648 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, a solution of the acetylsalicylic acid chloride (16 g, 0.08 moles) in toluene (50 ml) is added at the temperature of 5-10° C. under stirring. The mixture is maintained at a temperature within 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 solution of potassium carbonate at 25% w/v, with water, with a 3% hydrochloric acid solution, and lastly again with water, 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 within the
  2. stirringunder stirring for 2 hours
  3. extractionextracted with dichloromethane (2×100 ml) The organic phase
  4. customis separated
  5. washwashed in sequence with a solution of potassium carbonate at 25%
  6. customthe solvent evaporated under vacuum
  7. customThe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-10aaf4ab0d3e40c78af209d9f51044a8
Source dataset
uspto-grants-2008_05
Patent number
US07378437B2

Reaction notes

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