Sodium hydride → HCID 13013062, compound

HRID 1194807Notes

Reaction equation

HRID 1194807 reaction equation
[Cl-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[H][H].[OH:11][C:12]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]>O1CCCC1.O>[OH:15][CH:14]1[C:13]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:12]=2[O:11][CH2:2]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 612002-Hydroxy-4-methylbenzaldehydeHCID 197819Trimethyloxosulphonium chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 13013062HCID 13013062, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trimethylsulfoxonium chloride (12.9 g) in tetrahydrofuran (200 ml) was added sodium hydride (2.4 g of 100%). This solution was heated at reflux until hydrogen evolution had ceased. 13.6 g of 2-hydroxy-4-methylbenzaldehyde dissolved in tetrahydrofuran (100 ml) was then added. The reaction mixture was refluxed until the reaction was complete (3 hours). It was then poured into water (600 ml), extracted with ether, the ether dried over sodium sulphate and evaporated to give 3-hydroxy-6-methyl-2,3-dihydrobenzofuran.

Workup

  1. temperatureThis solution was heated
  2. additionwas then added
  3. temperatureThe reaction mixture was refluxed until the reaction
  4. custom(3 hours)
  5. extractionextracted with ether
  6. dry with materialthe ether dried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-16e05b46acfe44c8b47b3c671b1a0282
Source dataset
uspto-grants-1989_03
Patent number
US04816473

Reaction notes

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