3,4-dihydro-2H-pyran → 2-(3,4-Dimethoxyphenoxy)oxane

HRID 485176Notes

Reaction equation

HRID 485176 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>Cl.CCOCC>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 162513,4-Dimethoxyphenol

Product 1

HCID 202715542-(3,4-Dimethoxyphenoxy)oxane

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

3,4-Dimethoxyphenol (30.8 g) was added in small portions to a mixture of dihydropyran (29.2 ml) and conc. hydrochloric acid (3 drops) under nitrogen so that the temperature did not rise above 50° C. After the addition was complete the dark solution was stirred at room temperature for 3 hrs. and then diluted with ether. The resulting solution was washed with water, 2 N sodium hydroxide solution, water, dried (sodium sulphate) and evaporated to give 3,4-dimethoxyphenol tetrahydropyranyl ether.

Workup

  1. customdid not rise above 50° C
  2. additionAfter the addition
  3. washThe resulting solution was washed with water, 2 N sodium hydroxide solution, water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-e8e23e4b794346f2a6fa7982d60d24d7
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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