3-Methoxyphenol → HCID 10060488, 화합물

HRID 1063828노트

반응식

HRID 1063828 반응식
[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

참가 물질

5

반응물 2

HCID 90073-MethoxyphenolHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 10060488HCID 10060488, 화합물수율 24,786.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 80803,4-dihydro-2H-pyran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-82a9d0b28638495f904dab2427989a8e
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967201B1

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