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

HRID 2254212

反応式

HRID 2254212 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eb198cc73bb849c6bb61984f9f1c54f5
出典データセット
uspto-grants-1993_08
特許番号
US05234951

関連ノート

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