Chloromethyl Methyl Ether → 4-(Methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde

HRID 2254212

반응식

HRID 2254212 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C.[CH3:24][O:25][CH2:26]Cl>O1CCCC1>[CH3:24][O:25][CH2:26][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 4438533-Dimethylallyl-4-hydroxybenzaldehyde

생성물 1

HCID 145597524-(Methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde수율 91.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Then, 7.0 g of the so-obtained 4-hydroxy-3-(3-methyl-2-butenyl)benzaldehyde was dissolved in 70 ml of tetrahydrofuran, and 19.25 g of N,N-diisopropylethylamine was added to the solution and the mixture was stirred at room temperature for 1 hour. After the reaction, the reaction liquid was cooled to 0° C. and 7.0 ml of chloromethyl methyl ether was dropped into the reaction liquid, and the mixture was stirred at room temperature overnight. Then, the reaction liquid was poured into ice water, and the organic layer was extracted with ether, washed with water, dried with anhydrous sodium sulfate, and filtered. The obtained residue was subjected to the column chromatography (260 g of 200-400 mesh Kieselgel 60, hexane/ethyl acetate=6/1, 0.4 kg/cm2), fractions of 50 ml were recovered in sequence, and the 14th to 24th fractions were combined to obtain 7.85 g (yield=91.1%) of 4-methoxymethoxy-3-(3-methyl-2-butenyl)benzaldehyde in the form of a colorless liquid.

후처리

  1. customAfter the reaction
  2. customthe reaction liquid
  3. temperaturewas cooled to 0° C.
  4. stirringthe mixture was stirred at room temperature overnight
  5. customThen, the reaction liquid
  6. extractionthe organic layer was extracted with ether
  7. washwashed with water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customwere recovered in sequence

출처 및 근거

ORD 기록
ord-eb198cc73bb849c6bb61984f9f1c54f5
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05234951

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