Methanol → Benzene-1,3,5-tricarboxaldehyde

HRID 1503088Notes

Reaction equation

HRID 1503088 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[C:5]([CH2:11][OH:12])[CH:4]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CO>C(Cl)Cl.CC(C)=O>[CH:9]([C:7]1[CH:6]=[C:5]([CH:11]=[O:12])[CH:4]=[C:3]([CH:2]=[O:1])[CH:8]=1)=[O:10]

Participants

6

Reactant 3

HCID 887MethanolHCID 27480481,3,5-BenzenetrimethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 2747968Benzene-1,3,5-tricarboxaldehydeYield 33%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent3×

Procedure

1,3,5-Tris(hydroxymethyl)benzene 15 (927 mg, 5.12 mmol) was suspended in CH2Cl2 (25 mL) and solid PCC (5.94 g, 27.6 mmol) was added. After 30 minutes of stirring, the reaction was diluted with acetone (10 mL) and was allowed to stir for 3 hr at RT. TLC (10% MeOH, 90% CH2Cl2 Rf=0.50) was used to determine if the reaction was complete. After the reaction was complete, the precipitated chromium salts were filtered off and washed with CH2Cl2. The aqueous layer was extracted 3 times in CH2Cl2 and saturated Na2CO3. The organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated. Flash column chromatography (100% CH2Cl2 Rf=0.4) gave 16 (272 mg, 1.68 mmol, 33%). 1H NMR (CDCl3): δ 10.21 (s, 3H), 8.63 (s, 3H).

Workup

  1. stirringto stir for 3 hr at RT
  2. filtrationthe precipitated chromium salts were filtered off
  3. washwashed with CH2Cl2
  4. extractionThe aqueous layer was extracted 3 times in CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5e0b93f2267d4e1782d5563e6ace1c5e
Source dataset
uspto-grants-2015_12
Patent number
US09212131B2

Reaction notes

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