Formaldehyde → HCID 58041020, compound

HRID 2365782Notes

Reaction equation

HRID 2365782 reaction equation
C=O.[Cl-].[Mg+2].[Cl-].[Br:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[OH:15].C[CH2:17][O:18]CC>C1COCC1>[Br:6][C:7]1[C:8]([OH:15])=[C:9]([CH:10]=[C:11]([S:13][CH3:14])[CH:12]=1)[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 5360315Magnesium ChlorideHCID 54344931HCID 54344931, compound

Product 1

HCID 58041020HCID 58041020, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous paraformaldehyde (2.14 g) and anhydrous magnesium chloride (−10 mesh, 99.9%, 4.53 g) were suspended in anhydrous THF (120 mL) under nitrogen atmosphere. Freshly distilled TEA (6.7 mL) was added to the above suspended solution and stirred for 30 minutes. To the above mixture, a solution of 2-bromo-4-methylthiophenol (XXI, 5.22 g) in anhydrous THF (40 mL) was added. The resultant mixture was heated at gentle reflux and stirred for 6 h. After the mixture was cooled down to ambient temperature, ether (100 ml) was added. The organic layer was washed with 1N HCl (60 mL×3) and water (60 mL×3), and dried over MgSO4, filtered and solvent removed in vacuo. The mixture was recrystallized from hexane to afford the product (3.60 g, 61%) as a yellow solid.

Workup

  1. temperatureat gentle reflux
  2. stirringstirred for 6 h
  3. washThe organic layer was washed with 1N HCl (60 mL×3) and water (60 mL×3)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent removed in vacuo
  7. customThe mixture was recrystallized from hexane

Sources & evidence

ORD record
ord-c5a19e1bd51e40bfa3c82ddc51dd5551
Source dataset
uspto-grants-2014_04
Patent number
US08697720B2

Reaction notes

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