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

HRID 974111
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인쇄 미리보기

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HRID 974111 반응식
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
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1140
Toluene
용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-006c2c158d514df4be890a0b5949011c
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05066825

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