Acetic Anhydride → HCID 19822179, compound

HRID 1030395Notes

Reaction equation

HRID 1030395 reaction equation
[OH:1][C:2]1[C:3]([CH3:30])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:25][CH:26]([CH3:28])[CH3:27])([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)[CH2:6][C:5]2=[O:29].[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[C:31]([O:1][C:2]1[C:3]([CH3:30])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:25][CH:26]([CH3:28])[CH3:27])([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)[CH2:6][C:5]2=[O:29])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19822221HCID 19822221, compound

Product 1

HCID 19822179HCID 19822179, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.5 g of 6-hydroxy-2-isobutyl-5,7,8-trimethyl-2-(4-nitrophenoxymethyl)chroman-4-one (prepared as described in Preparation 6) and 30 ml of pyridine was mixed with 3 g of acetic anhydride and stirred for 35 hours at room temperature. The reaction mixture was then condensed by evaporation under reduced pressure, mixed with water and extracted with ethyl acetate and benzene. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, using a 5:1 by volume mixture of hexane and ethyl acetate, to give the title compound.

Workup

  1. customcondensed
  2. customby evaporation under reduced pressure
  3. additionmixed with water
  4. extractionextracted with ethyl acetate and benzene
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e853792376994b4d946baa032322db05
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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