MAGNESIUM SILICATE (synthetic) → 3-Benzylmercapto-4-carbomethoxy benzaldehyde

HRID 2072303

Reaction equation

HRID 2072303 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[C:17]([O:19][CH3:20])=[O:18])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-][Si]([O-])=O.[Mg+2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[C:17]([O:19][CH3:20])=[O:18])[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 54409048HCID 54409048, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 538686323-Benzylmercapto-4-carbomethoxy benzaldehydeYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 30 g 3-benzylmercapto-4-carbomethoxy benzyl alcohol in 900 ml of methylene chloride is stirred with 60 g of Florisil (activated magnesium silicate) in 900 ml of methylene chloride. To the thus-obtained slurry is added 39 g of solid pyridinium chlorochromate and the black reaction mixture obtained is stirred for 3-4 hours at room temperature, filtered over Celite (diatomaceous earth), and washed with 600 ml of methylene chloride. The methylene chloride filtrate is stirred overnight with a solution of 14 g of potassium hydroxide in 500 ml of water which removes all the dark color from the organic layer. The methylene chloride layer is separated, washed with 100 ml of 2N hydrochloric acid and then with 300 ml of water, dried over sodium sulfate and evaporated to dryness to yield 27.5 g of 3-benzylmercapto-4-carbomethoxy benzaldehyde having a melting point of 91°-93° C.

Workup

  1. customthe black reaction mixture obtained
  2. filtrationfiltered over Celite (diatomaceous earth)
  3. washwashed with 600 ml of methylene chloride
  4. stirringThe methylene chloride filtrate is stirred overnight with a solution of 14 g of potassium hydroxide in 500 ml of water which
  5. customremoves all the dark color from the organic layer
  6. customThe methylene chloride layer is separated
  7. washwashed with 100 ml of 2N hydrochloric acid
  8. dry with materialwith 300 ml of water, dried over sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-c551f243a2d34fb99464f955c13eb4cb
Source dataset
uspto-grants-1977_09
Patent number
US04051148

Linked notes

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