3-Methoxyphenol → HCID 10060488, compound

HRID 1824915Notes

Reaction equation

HRID 1824915 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[OH2:10].[C:11]1(C)C=[CH:15][C:14](S(O)(=O)=O)=[CH:13][CH:12]=1>O1C=CCCC1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][CH:15]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 90073-MethoxyphenolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10060488HCID 10060488, compoundYield 24,786.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80803,4-dihydro-2H-pyranSolvent2×

Procedure

A solution of 22 gm (177.4 mMol) 3-methoxyphenol in 30 mL dihydropyran was added dropwise to a solution of 100 mg (0.525 mMol) p-toluenesulfonic acid monohydrate in 10 mL dihydropyran while cooling in an ice/water bath. After stirring for 1 hour the reaction mixture was diluted with 300 mL diethyl ether and then washed sequentially with 100 mL 0.1 N sodium hydroxide and 100 mL saturated aqueous sodium chloride. The remaining organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The resulting oil was distilled. The fraction distilling at 110–130° C. was collected and then partitioned between 5 N sodium hydroxide and diethyl ether. The organic phase was separated, washed sequentially with water and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to provide 27.1 gm (73%) of tetrahydropyran-2-yl 3-methoxyphenyl ether.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. washwashed sequentially with 100 mL 0.1 N sodium hydroxide and 100 mL saturated aqueous sodium chloride
  3. dry with materialThe remaining organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationThe resulting oil was distilled
  6. distillationThe fraction distilling at 110–130° C.
  7. customwas collected
  8. custompartitioned between 5 N sodium hydroxide and diethyl ether
  9. customThe organic phase was separated
  10. washwashed sequentially with water and saturated aqueous sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62325daec82046659f6c20f0cf33cd8c
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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