Acetic Anhydride → HCID 9865661, compound

HRID 1589697Notes

Reaction equation

HRID 1589697 reaction equation
[OH:1][C:2]1[C:3]([CH3:26])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:25])([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][CH2:5]2.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:1][C:2]1[C:3]([CH3:26])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:25])([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][CH2:5]2)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 134888696-Hydroxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman

Product 1

HCID 9865661HCID 9865661, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20.4 g of 6-hydroxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman were dissolved in 60 ml of pyridine, and, while stirring, 30 ml of acetic anhydride were added dropwise at 10° C. The mixture was gradually restored to room temperature and then reacted for 1 hour at 30° C. The reaction mixture was cooled and then poured into ice-water and extracted with a 1:1 by volume mixture of benzene and cyclohexane. The extract was washed well with a 2% w/v aqueous solution of hydrochloric acid and then with water, after which it was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, giving the desired 6-acetoxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman. Rf value on thin layer chromatography: 0.64 [silica gel; developing solvent; benzene and ethyl acetate=10:1 by volume]

Workup

  1. customwas gradually restored to room temperature
  2. customreacted for 1 hour at 30° C
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with a 1:1 by volume mixture of benzene and cyclohexane
  5. washThe extract was washed well with a 2% w/v aqueous solution of hydrochloric acid
  6. dry with materialwith water, after which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-852bfe20320d4c469e74b5bdcfdeb0de
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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