Hydrochloric Acid → 4-(Methoxymethoxymethyl)-2-methylbenzaldehyde

HRID 501792노트

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HRID 501792 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]=1[CH3:13].CN(C)[CH:16]=[O:17].O.Cl>O1CCCC1.C([Li])CCC.CCCCCC>[CH3:12][O:11][CH2:10][O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:16]=[O:17])=[C:3]([CH3:13])[CH:4]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 684578621-Bromo-4-((methoxymethoxy)methyl)-2-methylbenzene

생성물 1

HCID 230215454-(Methoxymethoxymethyl)-2-methylbenzaldehyde

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 178418339Butyllithium용매

반응 조건

온도
-65 °C

실험 절차

4.00 g of 1-bromo-4-[(methoxymethoxy)methyl]-2-methylbenzene was dissolved in 40 mL of tetrahydrofuran, to which 11.5 mL of a solution of n-butyllithium in n-hexane (1.56 M) was added dropwise at −65 to −60° C., and then this mixture was stirred for 30 minutes at −65° C. Then, 20 mL of N,N-dimethylformamide was added dropwise thereto at −65 to −40° C., and a temperature of this reaction mixture was raised to room temperature over one hour and was stirred for another one hour at room temperature. Water was added to the reaction mixture and adjusted to pH 5 with 6M hydrochloric acid, followed by addition thereto of ethyl acetate, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 1.54 g of 4-[(methoxymethoxy)methyl]-2-methylbenzaldehyde as colorless oil.

후처리

  1. additionwas added dropwise at −65 to −60° C.
  2. temperatureat −65 to −40° C., and a temperature of this reaction mixture was raised to room temperature over one hour
  3. stirringwas stirred for another one hour at room temperature
  4. additionfollowed by addition
  5. customof ethyl acetate, and then the organic phase was separated
  6. washAfter the resultant organic phase was washed with water
  7. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled out under reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

출처 및 근거

ORD 기록
ord-e4c1dba4962a48189a403b9116c41837
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772285B2

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