Salicylic Acid → HCID 67120996, compound

HRID 1694782Notes

Reaction equation

HRID 1694782 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-bdc41944d0624845aad67ddff0e2ba33
Source dataset
uspto-grants-2012_04
Patent number
US08158838B2

Reaction notes

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