(3-Bromopropyl)benzene → HCID 10937342, compound

HRID 274538Notes

Reaction equation

HRID 274538 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])(C)(C)C.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][C:25]=1[O:32][CH3:33])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC.CCCCC>[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]([OH:29])[CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:26][C:25]=1[O:32][CH3:33])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 10937342HCID 10937342, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Procedure

A solution of 20.0 g of 3-phenylpropyl bromide in 300 ml of ether is treated at -60° while stirring within 15 minutes with a solution of 71.8 ml of tert.butyllithium (1.4 molar) in pentane. After 10 minutes there is added dropwise at this temperature within 15 minutes a solution of 22.14 g of vanillin benzyl ether in 200 ml of ether, whereupon the mixture is stirred for an additional 2 hours. The mixture is poured into 11 of ice-water and extracted three times with 500 ml of ethyl acetate each time. The organic phase is washed twice with 200 ml of water each time, dried over sodium sulfate and evaporated. The oil obtained is chromatographed on 1 kg of silica gel with methylene chloride. The crystals obtained are recrystallized from ether/pentane. There is obtained 4-(benzyloxy)-3-methoxy-α-(3-phenylpropyl)benzyl alcohol in the form of colorless crystals of m.p. 71°-73°.

Workup

  1. extractionextracted three times with 500 ml of ethyl acetate each time
  2. washThe organic phase is washed twice with 200 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe oil obtained
  6. customis chromatographed on 1 kg of silica gel with methylene chloride
  7. customThe crystals obtained
  8. customare recrystallized from ether/pentane

Sources & evidence

ORD record
ord-5fb2bd81f3044d8b9abd2f55ad9efbe6
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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