Trimethyl orthoformate → Ethyl 3-dimethoxymethyl-4-methoxybenzoate

HRID 558434

반응식

HRID 558434 반응식
C([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.[CH:16]([O:21][CH3:22])([O:19][CH3:20])OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH3:22][O:21][CH:16]([O:19][CH3:20])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

6

반응물 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 638670Ethyl 3-formyl-4-methoxybenzoate

생성물 1

HCID 23141411Ethyl 3-dimethoxymethyl-4-methoxybenzoate수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Ethyl 3-formyl-4-methoxybenzoate (500 mg) obtained in step C of Example 1-2-1 was dissolved in 10 mL of methanol. Trimethyl orthoformate (263 μL) and 41 mg of p-toluenesulfonic acid monohydrate were added to the solution, and then the mixture was heated for 2 hours under reflux. After the reaction solution was cooled, 5 mL of a saturated aqueous solution of sodium bicarbonate was added, and the resulting mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with purified water and then with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, whereafter the filtrate was concentrated under reduced pressure. The residue was dried under reduced pressure to obtain 596 mg (97%) of ethyl 3-dimethoxymethyl-4-methoxybenzoate.

후처리

  1. temperaturethe mixture was heated for 2 hours
  2. temperatureunder reflux
  3. temperatureAfter the reaction solution was cooled
  4. concentrationthe resulting mixture was concentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with purified water
  7. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  8. customThe anhydrous sodium sulfate was separated by filtration, whereafter the filtrate
  9. concentrationwas concentrated under reduced pressure
  10. customThe residue was dried under reduced pressure

출처 및 근거

ORD 기록
ord-48dbf8b5698148bba2bc54c8f0b52c3a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063046B2

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