Acetone → 2,2-DIMETHYL-4-OXOCHROMAN-6-CARBOXYLIC ACID

HRID 635906Notes

Reaction equation

HRID 635906 reaction equation
N1C[CH2:4][CH2:3][CH2:2]1.CC(C)=O.[C:10]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[OH:22])[C:16]([OH:18])=[O:17])(=[O:12])[CH3:11]>C(#N)C>[C:16]([C:15]1[CH:14]=[C:13]2[C:21](=[CH:20][CH:19]=1)[O:22][C:3]([CH3:4])([CH3:2])[CH2:11][C:10]2=[O:12])([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 91792453-Acetyl-4-hydroxybenzoic acid

Product 1

HCID 117461302,2-DIMETHYL-4-OXOCHROMAN-6-CARBOXYLIC ACID

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.8 g of pyrrolidine and 40 ml of acetone are added to a suspension of 14.7 g (0.0815 mol) of 3-acetyl-4-hydroxybenzoic acid in 200 ml of acetonitrile. The slowly discoloring solution is allowed to stand at room temperature for 2 days, the solvent is distilled off on a rotary evaporator, the residue is treated with water and adjusted to acidic pH<1 using conc. hydrochloric acid and the crystalline substance is filtered off.

Workup

  1. distillationthe solvent is distilled off on a rotary evaporator
  2. additionthe residue is treated with water and adjusted to acidic pH<1
  3. filtrationthe crystalline substance is filtered off

Sources & evidence

ORD record
ord-45970c8c85c1410e9f0f0370699209ed
Source dataset
uspto-grants-2001_02
Patent number
US06191164B1

Reaction notes

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