p-Toluenesulfonic acid → HCID 21220841, compound

HRID 1584789Notes

Reaction equation

HRID 1584789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:24](O)[CH2:25][CH2:26][OH:27]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[O:27][CH2:26][CH2:25][CH2:24][O:12]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 212208405-Bromo-1-benzofuran-7-carbaldehyde

Product 1

HCID 21220841HCID 21220841, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-benzofuran-7-carbaldehyde (400 mg), 4-methylphenylsulphonic acid (0.38 g) and 1,3-propanediol (10 ml) in toluene (15 ml) was heated at reflux for 19 h, with azeotropic removal of water by Dean-Stark Apparatus. The reaction mixture was cooled, diluted with water (80 ml) and extracted with toluene (30 ml). The organic phase was dried, filtered and the filtrate evaporated in vacuo to give a brown oil. Purification by FCC eluted with hexane:ethyl acetate (7:1→3:1) gave the title compound as a yellow solid (427 mg).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with toluene (30 ml)
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customto give a brown oil
  8. customPurification by FCC
  9. washeluted with hexane:ethyl acetate (7:1→3:1)

Sources & evidence

ORD record
ord-dff727f3609941ad817f819b763562ab
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

Loading…