Acetic Anhydride → HCID 13605827, compound

HRID 1030424Notes

Reaction equation

HRID 1030424 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 (prepared as described in Preparation 53), 1 ml of acetic anhydride and 10 ml of pyridine was allowed to stand for 1 day at room temperature. The reaction mixture was then poured into ice-water, stirred for 2 hours and extracted with benzene. The benzene extract was washed with 3N aqueous hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and water in that order, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was recrystallized from a mixture of benzene and ethyl acetate (about 10:1 by volume) to give the title compound, melting at 82°-84° C.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. washwas washed with 3N aqueous hydrochloric acid, water
  4. dry with materiala saturated aqueous solution of sodium bicarbonate and water in that order, and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was recrystallized from a mixture of benzene and ethyl acetate (about 10:1 by volume)

Sources & evidence

ORD record
ord-75984e321e7948b8922285215dbe8da0
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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