3-Hydroxybenzyl alcohol → Aspirin

HRID 2122060Notes

Reaction equation

HRID 2122060 reaction equation
[OH:1]CC1C=C(O)C=CC=1.[C:10]([O:13][C:14]1[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:16](Cl)=[O:17])(=[O:12])[CH3:11]>[Na+].[OH-].ClCCl>[C:10]([O:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:1])=[O:17])(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 1023-Hydroxybenzyl alcoholHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 2244AspirinYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-hydroxymethylphenol (25.25 g, 0.2 moles) is dissolved in a 5% hydroxide sodium solution (160 ml). To the so obtained solution an acetylsalicylic acid chloride solution (40.4 g, 0.2 moles) in dichloromethane (50 ml) is added at roam temperature, under stirring. The mixture is maintained at room temperature under stirring for 2 hours and then extracted with dichloromethane (2×100 ml). The organic phase is separated, anhydrified with sodium sulphate and the solvent evaporated under vacuum. The residue is crystallized from a mixture of ethyl acetate and hexane. 3-hydroxymethylphenyl ester of the 2-acetoxybenzoic acid (45.8 g, 0.16 moles, yield 80%) is obtained.

Workup

  1. stirringunder stirring for 2 hours
  2. extractionextracted with dichloromethane (2×100 ml)
  3. customThe organic phase is separated
  4. customthe solvent evaporated under vacuum
  5. customThe residue is crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-cc238c1a6532475ca2e1846dd4280340
Source dataset
uspto-grants-2004_02
Patent number
US06696591B1

Reaction notes

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