Acetone → 68454-18-2

HRID 1154859Notes

Reaction equation

HRID 1154859 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].CC(C)=O.[OH:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([CH3:22])=[CH:16][C:17](=[O:21])[O:18]2)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.[I-].[K+]>[CH2:2]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([CH3:22])=[CH:16][C:17](=[O:21])[O:18]2)=[CH:13][CH:12]=1)[C:3]([CH3:4])=[O:5]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 52805674-Methylumbelliferone

Product 1

HCID 87936168454-18-2Yield 97.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of chloroacetone (26.23 mL, 30.48 g, 0.329 mol), potassium iodide (1.0 g, 6 mmol), and reagent grade acetone (dried over K2CO3, ca. 400 mL) was allowed to stand for 151/2 hours. 7-Hydroxy-4-methylcoumarin (50.0 g, 0.284 mol), anhyd. K2CO3 (45.50 g, 0.321 mol), and dry reagent grade acetone (1 L) were added and the mixture was refluxed for 24 hours with overhead stirring. The hot mixture was filtered and the precipitate was washed with acetone. The washes and the filtrate were combined and evaporated in vacuo to obtain a yellow solid, which dissolved in CHCl3 (1.3 L). The CHCl3 solution was extracted once with 5% aq. NaOH (500 mL), washed with two portions (500 mL) of water, dried (MgSO4), and evaporated in vacuo to obtain 7-acetonyloxy-4-methylcoumarin (64.30 g, 97.5%), mp 146.0°-148.0° C. Recrystallization of 61.82 g from 95% ethanol gave a purer product (53.91 g, 87% recovery, 85% yield), mp 150.1°-151.2° C.

Workup

  1. custom2 hours
  2. temperaturethe mixture was refluxed for 24 hours with overhead stirring
  3. filtrationThe hot mixture was filtered
  4. washthe precipitate was washed with acetone
  5. customevaporated in vacuo
  6. customto obtain a yellow solid, which
  7. extractionThe CHCl3 solution was extracted once with 5% aq. NaOH (500 mL)
  8. washwashed with two portions (500 mL) of water
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-e190e0e334de4cabb7c3f0a0ea5a3e79
Source dataset
uspto-grants-1981_11
Patent number
US04298614

Reaction notes

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