Benzaldehyde → HCID 2760079, compound

HRID 1898956Notes

Reaction equation

HRID 1898956 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[Mg].II.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)C.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:13]([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 807IodineHCID 660374-BromothioanisoleHCID 5462224Magnesium2×

Product 1

HCID 2760079HCID 2760079, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromophenyl methyl sulfide (Aldrich) (3.3 g, 16.4 mmol) in 10 mL of dry diethyl ether is slowly added to a stirred suspension of magnesium turnings (0.44 g, 18.1 mmol) and three crystals of iodine in 10 mL of boiling dry diethyl ether. The reaction is heated at reflux for several hours until almost all the magnesium is consumed. The reaction is cooled to room temperature, and a solution of benzaldehyde (2.0 mL, 19.7 mmol) in 50 mL of dry diethyl ether is added dropwise. The reaction mixture is diluted with ethyl acetate and washed twice with 1N HCl, followed by saturated aqueous sodium bicarbonate, and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude solid is crystallized from diethyl ether/hexane to give 2.4 g (64%) of 4-methylthiobenzhydrol: melting point 92°-93.5° C.

Workup

  1. temperatureThe reaction is heated
  2. customis consumed
  3. washwashed twice with 1N HCl
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude solid is crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-da8c5d3bdffc4b9fb6cf04188b2d7dcd
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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