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

HRID 501792ノート

反応式

HRID 501792 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 230215454-(Methoxymethoxymethyl)-2-methylbenzaldehyde

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 178418339Butyllithium溶媒

反応条件

温度
-65 °C

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-e4c1dba4962a48189a403b9116c41837
出典データセット
uspto-grants-2010_08
特許番号
US07772285B2

反応ノート

読み込み中…