3,4-Dihydroxybenzaldehyde → HCID 11052728, compound

HRID 1048737Notes

Reaction equation

HRID 1048737 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH3:11][C:12]([CH3:16])=[CH:13][CH:14]=O>N1C=CC=CC=1.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[C:8]2[C:9]=1[O:10][C:12]([CH3:16])([CH3:11])[CH:13]=[CH:14]2

Participants

5

Reactant 2

HCID 87683,4-DihydroxybenzaldehydeHCID 610203-Methyl-2-butenal

Product 1

HCID 11052728HCID 11052728, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3,4-Dihydroxybenzaldehyde (2.3 g, 17 mmol) and 3-methylbut-2-enal (1 mL, 10 mmol) were dissolved in 3 mL of pyridine and refluxed overnight. Pyridine was evaporated under vacuum, and the crude reaction mixture was dissolved in methylene chloride. 9 (103 mg, 2.4%) was purified with silica gel chromatography with ethyl acetate/hexane (1/50). 1H NMR (CDCl3): δ 1.50 (s, 6H), 5.70 (d, J=10.1 Hz, 1H), 6.38 (d, J=10.1 Hz, 1H), 7.15 (d, J=2.14 Hz, 1H), 7.32 (d, J=1.83 Hz, 1H), 9.78 (s, 1H).

Workup

  1. temperaturerefluxed overnight
  2. customPyridine was evaporated under vacuum
  3. customthe crude reaction mixture
  4. custom9 (103 mg, 2.4%) was purified with silica gel chromatography with ethyl acetate/hexane (1/50)

Sources & evidence

ORD record
ord-c182579a2fbc47eca7e31a6094dbe37f
Source dataset
uspto-grants-2016_07
Patent number
US09381260B2

Reaction notes

Loading…