Acetic Anhydride → HCID 53234289, compound

HRID 239607Notes

Reaction equation

HRID 239607 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[C:18](OC(=O)C)(=O)[CH3:19].C([O-])(=O)C.[Na+]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:17][C:18]([CH3:19])=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]2=[O:16]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 12209494HCID 12209494, compound

Product 1

HCID 53234289HCID 53234289, compoundYield 97%

Procedure

Intermediate 1 (8.9 g, 30.56 mmoles) was taken in a RB flask and to this acetic anhydride (59 ml) and sodium acetate (17.5 g, 213 mmoles) were added and the mixture was refluxed for 12 h. After cooling to RT, the reaction mixture was quenched by the addition of ice cold water. The solid formed was filtered and washed with water. The product was dried under vacuum to afford the title compound as white solid (9.4 g, 97% yield). MP: 119-121° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 8.35(d, J=2.4 Hz, 1H), 7.75(dd, J=11.3, 2.4 Hz, 1H), 7.46(t, 2H), 7.39(d, J=7.2 Hz, 1H), 7.36(d, J=8.8 Hz, 1H), 7.28(m,2H), 2.32(s, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 12 h
  3. customthe reaction mixture was quenched by the addition of ice cold water
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-b04adb128f58470580b3c7d0ac4206f2
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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