Acetic Anhydride → HCID 13605827, compound

HRID 1589707Notes

Reaction equation

HRID 1589707 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:27])[CH2:10][C:11]([CH3:26])([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[O:12]2)=[CH:7][C:6]=1[OH:28])([CH3:4])([CH3:3])[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([O:28][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])[O:12][C:11]([CH3:26])([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[CH2:10][C:9]2=[O:27])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13605826HCID 13605826, compound

Product 1

HCID 13605827HCID 13605827, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.7 g of 7-t-butyl-6-hydroxy-2-methyl-2-(4-nitrophenoxymethyl)chroman-4-one, 1 ml of acetic anhydride and 10 ml of pyridine was allowed to stand at room temperature for 1 day. The reaction mixture was then poured into ice-water and stirred for 2 hours, and the crude substance was extracted with benzene. The organic solution was washed successively with 3N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and water, and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the crude product thus obtained was recrystallized from a 10:1 by volume mixture of benzene and ethyl acetate, to give the desired 6-acetoxy-7-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)chroman-4-one.

Workup

  1. extractionthe crude substance was extracted with benzene
  2. washThe organic solution was washed successively with 3N hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and water, and dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe crude product thus obtained
  6. customwas recrystallized from a 10:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-f351234937054cfaa95caf8862d36ab6
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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