Sulfuric Acid → HCID 18421402, compound

HRID 368788Notes

Reaction equation

HRID 368788 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:29])=[C:10]([CH2:17][N:18]3[C:22](=[O:23])[C:21]4=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]4[C:19]3=[O:28])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=O)C.OS(O)(=O)=O>CO>[OH:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:29])=[C:10]([CH2:17][N:18]3[C:19](=[O:28])[C:20]4=[CH:27][CH:26]=[CH:25][CH:24]=[C:21]4[C:22]3=[O:23])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18421446HCID 18421446, compound

Product 1

HCID 18421402HCID 18421402, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-acetoxy-4,8-dimethyl-3-phthalimidomethylcoumarin (15.9 g, 40.6 mol) was stirred in methanol (2000 mL) while concentrated H2SO4 (75 mL) was added dropwise. The resulting mixture was refluxed for 3 hours, allowed to cool to room temperature, then chilled in an ice water bath. The precipitate was collected in a Buchner funnel and rinsed with ice cold methanol to give 7-hydroxy-4,8-dimethyl-3-phthalimidomethylcoumarin, a white solid (12.1 g, 85.6%). 1H NMR (CD3OD): δ 7.87-7.78 (m, 4H), 7.55 (d, J=8.7 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 2.61 (s, 3H), 2.23 (s, 3H), the methylene peak is presumably obscured by solvent hydroxy peak at 4.88.

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. temperaturechilled in an ice water bath
  4. customThe precipitate was collected in a Buchner funnel
  5. washrinsed with ice cold methanol

Sources & evidence

ORD record
ord-e2f91c8b07b544dd813a954b55b0f786
Source dataset
uspto-grants-2000_10
Patent number
US06133460

Reaction notes

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