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Water → 2-(3,4-Dimethoxy-alpha-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal

HRID 974111
ノート
印刷プレビュー

反応式

HRID 974111 の反応式
C([Li])CCC.[CH3:6][O:7][CH:8]([O:21][CH3:22])[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH:28]=[O:29].O>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH3:22][O:21][CH:8]([O:7][CH3:6])[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[C:10]=1[CH:28]([OH:29])[C:27]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:25]([O:24][CH3:23])[CH:26]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 8419VeratraldehydeHCID 41935783,4,5-Trimethoxybenzaldehyde dimethyl acetalHCID 178418339Butyllithium

生成物 1

HCID 105975732-(3,4-Dimethoxy-alpha-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal収率 97.4%

試薬・触媒・溶媒 3

HCID 1140
Toluene
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

136 ml of a 1.6M n-butyl lithium solution in toluene are added to a solution of 48.5 g of 3,4,5-trimethoxybenzaldehyde dimethyl acetal in 485 ml of tetrahydrofuran under stirring at 0° C. for about 20 minutes. The mixture is further stirred at 0° C. for 30 minutes, and 33.2 g of 3,4-dimethoxybenzaldehyde are added thereto. After stirring the mixture at 0° to 10° C. for 2 hours, 780 ml of water and 780 ml of ethyl acetate are added thereto. After shaking the mixture, the organic layer is separated therefrom, washed with water and evaporated under reduced pressure to remove solvent. 79.5 g of 2-(3,4-dimethoxy-α-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal are thereby obtained as a yellow oil.

後処理

  1. stirringThe mixture is further stirred at 0° C. for 30 minutes
  2. stirringAfter stirring the mixture at 0° to 10° C. for 2 hours
  3. stirringAfter shaking the mixture
  4. customthe organic layer is separated
  5. washwashed with water
  6. customevaporated under reduced pressure
  7. customto remove solvent

出典と根拠

ORDレコード
ord-006c2c158d514df4be890a0b5949011c
出典データセット
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05066825

反応ノート

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