Acetic Acid → alpha-[4-(Benzyloxy)-3-methoxyphenyl]-4-quinolinemethanol

HRID 2254827Notes

Reaction equation

HRID 2254827 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[CH:7][CH:8]=1.[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[O:21])=[CH:12][CH:11]=1.O.[C:23]([OH:26])(=O)C.[CH3:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O1CCCC1>[CH2:1]([O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=[CH:11][CH:12]=2)[OH:21])=[CH:7][C:8]=1[O:26][CH3:23])[C:29]1[CH:28]=[CH:27][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8058HexaneHCID 169713-BromoanisoleHCID 780724-Quinolinecarboxaldehyde

Product 1

HCID 21459134alpha-[4-(Benzyloxy)-3-methoxyphenyl]-4-quinolinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

25 ml of tert.-butylithium solution (1.4M in hexane) are added dropwise at -70° within 10 minutes to 10 g of 4-benzyloxy)-3-methoxy-bromobenzene dissolved in 100 ml of tetrahydrofuran. After stirring at -70° for 1 hour, 5 g of quinoline-4-carbaldehyde dissolved in 50 ml of tetrahydrofuran are added dropwise within 30 minutes. The reaction mixture is stirred at -40° for 1 hour and at -5° for 1 hour, poured into 200 ml of water and adjusted to pH 4 with glacial acetic acid. The mixture is extracted three times with 50 ml of ether each time. The combined ether phases are washed with water, dried over sodium sulfate and evaporated. There is obtained α-[4(benzyloxy)-3-methoxyphenyl]-4-quinolinemethanol as an amorphous solid.

Workup

  1. additionare added dropwise within 30 minutes
  2. stirringThe reaction mixture is stirred at -40° for 1 hour and at -5° for 1 hour
  3. extractionThe mixture is extracted three times with 50 ml of ether each time
  4. washThe combined ether phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-c5f70cde50974a5ba373f05a4a6e38d8
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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