Acetic Acid → HCID 19884786, compound

HRID 846242Notes

Reaction equation

HRID 846242 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:17])[CH:10]([CH3:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.Br.C(O)(=O)C>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:17])[CH:10]([CH3:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 13693404HCID 13693404, compound

Product 1

HCID 19884786HCID 19884786, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the ester from Example 70, Step A (8.15 g), 48% HBr (40 ml) and acetic acid (80 ml) was refluxed for 4 days, then poured into water (250 ml) and extracted with ethyl acetate. The extracts were washed with water and dried (Na2SO4) and evaporated to an oil which was treated with 10% HCl in methanol (150 ml) for 18 hours. The volatiles were removed by evaporation and the residue was taken up in CH2Cl2, washed with water, brine, dried, evaporated to dryness then purified by chromatography on silica gel to provide the title compound, mp 89°-91° C.

Workup

  1. temperaturewas refluxed for 4 days
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to an oil which
  6. additionwas treated with 10% HCl in methanol (150 ml) for 18 hours
  7. customThe volatiles were removed by evaporation
  8. washwashed with water, brine
  9. customdried
  10. customevaporated to dryness
  11. customthen purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b2b1e18d777a401db5720b52e064d29c
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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