3-Benzyloxybenzaldehyde → 1-Benzyloxy-3-vinylbenzene

HRID 1106891Notes

Reaction equation

HRID 1106891 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([O:13][C:14]1[CH:15]=C(C=[CH:20][CH:21]=1)C=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH:3]([C:2]1[CH:1]=[CH:20][CH:21]=[C:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:15]=1)=[CH2:4]

Participants

5

Reactant 2

HCID 743423-BenzyloxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 121635051-Benzyloxy-3-vinylbenzene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyltriphenylphosphonium bromide (51 g, 143 mmol) in tetrahydrofuran (500 mL) under argon at -20° C. was added butyllithium (56 mL, 140 mmol) over 20 minutes. The reaction was stirred for 10 minutes, then 3-benzyloxybenzaldehyde (29 g, 137 mmol) in tetrahydrofuran (60 mL) was added over 15 minutes. The reaction was stirred for 6.5 hours and left to stand overnight. The solvent was decanted off and the residue dissolved in dichloromethane (100 mL) and extracted with a heptane/diethyl ether mixture (9:1) until all the product was removed. The combined organics were filtered through silica and the solvent removed in vacuo to give the product as a clear oil, 122 mmol, 89%.

Workup

  1. stirringThe reaction was stirred for 6.5 hours
  2. waitleft
  3. waitto stand overnight
  4. customThe solvent was decanted off
  5. dissolutionthe residue dissolved in dichloromethane (100 mL)
  6. extractionextracted with a heptane/diethyl ether mixture (9:1) until all the product
  7. customwas removed
  8. filtrationThe combined organics were filtered through silica
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a13b9e9099044b10a52a07c86e628f8a
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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