Sodium hydride → HCID 13013062, compound

HRID 868611Notes

Reaction equation

HRID 868611 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-d4ff755480ab4dd888fc5850a3b2990a
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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