Salicylic Acid → HCID 67120996, compound

HRID 2066051Notes

Reaction equation

HRID 2066051 reaction equation
C(O)(=O)C1C(=CC=CC=1)O.C(OO)(C)(C)C.C1(C)C=CC=CC=1.[C:24]1([S:30]([CH:33]([CH2:44][CH:45]=[C:46]([CH3:54])[CH2:47][CH2:48][CH:49]=[C:50]([CH3:53])[CH:51]=[O:52])[CH:34]=[C:35]([CH3:43])[CH2:36][CH2:37][CH:38]=[C:39]([CH3:42])[CH:40]=[O:41])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:24]1([S:30]([CH:33]([CH2:44][CH:45]=[C:46]([CH3:54])[CH2:47][CH2:48][CH:49]=[C:50]([CH3:53])[CH2:51][OH:52])[CH:34]=[C:35]([CH3:43])[CH2:36][CH2:37][CH:38]=[C:39]([CH3:42])[CH2:40][OH:41])(=[O:32])=[O:31])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 1140TolueneHCID 6410tert-Butyl hydroperoxideHCID 74325984HCID 74325984, compound

Product 1

HCID 67120996HCID 67120996, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of SeO2 (0.54 g, 4.82 mmol, 2 equiv) and salicylic acid (0.34 g, 2.41 mmol, 1 equiv) in CH2Cl2 (20 mL) at 0° C. was added a 3.0 M solution of t-butyl hydrogen peroxide (TBHP) in toluene (5.0 mL, 14.46 mmol, 6 equiv). The mixture was stirred at that temperature for 1.5 h, and a solution of the compound (J) (1.00 g, 2.41 mmol, 1 equiv) in CH.sub.2Cl.sub.2 (5 mL) was slowly added for 10 min. The reaction mixture was stirred at 0° C. for 3 h, diluted with CH2Cl2 (30 mL), washed with 10% NaOH solution (10 mL×3) and then saturated Na2S2O3 solution (10 mL×3), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the diol compound (K) (0.47 g, 1.06 mmol) in 44% yield, together with the hydroxyl-aldehyde (0.13 g, 0.29 mmol, 12% yield), which was derived from further oxidation. Both of these two compounds can provide the dialdehyde of the Chemical Formula 3 after the Swern oxidation reaction.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 3 h
  2. washwashed with 10% NaOH solution (10 mL×3)
  3. dry with materialsaturated Na2S2O3 solution (10 mL×3), dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f0f862842804f4f808e0eeb99f0d60d
Source dataset
uspto-grants-2012_10
Patent number
US08288605B2

Reaction notes

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