Diethyl Ether → HCID 11183157, compound

HRID 1981420Notes

Reaction equation

HRID 1981420 reaction equation
[CH2:1]([O:3]CC)[CH3:2].[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH3:16])[CH:8]=1.C(OC(=O)C)(=O)C>O>[C:1]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH3:16])[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 684754-Hydroxy-o-toluic acid

Product 1

HCID 11183157HCID 11183157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 40 ml of anhydrous ethyl ether, was dissolved 7.1 g of 4-hydroxy-2-methylbenzoic acid followed by 21.3 g of acetic anhydride. The solution was stirred for 2.4 hours at room temperature. The reaction mixture was freed from the solvent under reduced pressure. The residue was admixed with hot water, then allowed to cool, and extracted with ethyl ether. The organic layer was washed with 2% hydrochloric acid, dried over anhydrous magnesium sulfate, and freed from the solvent by distillation under reduced pressure. The residue was recrystallized from an ethyl ether-petroleum ether mixture to obtain 7.5 g of 4-acetyloxy-2-methylbenzoic acid.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl ether
  3. washThe organic layer was washed with 2% hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationfreed from the solvent by distillation under reduced pressure
  6. customThe residue was recrystallized from an ethyl ether-petroleum ether mixture

Sources & evidence

ORD record
ord-77bd16686a7d472f841c97c9b83d95d2
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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