Acetic Anhydride → HCID 53234289, compound

HRID 1476147Notes

Reaction equation

HRID 1476147 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=2.4Hz, 1H), 7.75 (dd, J=11.3, 2.4 Hz, 1H), 7.46 (t, 2H), 7.39 (d, J=7.2Hz, 1H), 7.36 (d, J=8.8Hz, 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-7aa40f0b282741a0877068d4202712b3
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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