Phenol → HCID 19437041, compound

HRID 1735168Notes

Reaction equation

HRID 1735168 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:15][C:16]1[O:21][CH2:20][CH2:19][CH2:18][CH:17]=1)(=O)=O>CN(C)C=O>[O:9]([CH2:15][C:16]1[O:21][CH2:20][CH2:19][CH2:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 15097264HCID 15097264, compound

Product 1

HCID 19437041HCID 19437041, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.0 g (0.25 mol) of sodium hydride are added a little at a time at room temperature to 20.5 g (0.22 mol) of phenol in 200 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, after which 42 g (0.22 mol) of 2,3-dihydropyran-6-ylmethyl methanesulfonate (Example 7b) are added dropwise with slight cooling. Stirring is carried out for 4 hours at room temperature, after which the reaction mixture is poured onto water. The aqueous phase is extracted three times with diethyl ether and the organic phase is dried over MgSO4 and evaporated down under reduced pressure. The residue is distilled. 27 g (0.14 mol=57%, based on 6-formyl-2,3-dihydropyran) of the title compound are obtained as a pale yellow oil.

Workup

  1. stirringStirring
  2. waitis carried out for 4 hours at room temperature
  3. additionafter which the reaction mixture is poured onto water
  4. extractionThe aqueous phase is extracted three times with diethyl ether
  5. dry with materialthe organic phase is dried over MgSO4
  6. customevaporated down under reduced pressure
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-bd504889e02d4373a543af384ffb563c
Source dataset
uspto-grants-1996_07
Patent number
US05536734

Reaction notes

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