Tetrahydrofuran → 3-Allyloxy-4-methoxystyrene

HRID 235611Notes

Reaction equation

HRID 235611 reaction equation
[NH2-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH:10]=O)[CH:4]=[CH2:5].O1CCC[CH2:18]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH:10]=[CH2:18])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24533Sodium amideHCID 5341483-Allyloxy-4-methoxybenzaldehyde

Product 1

HCID 198314233-Allyloxy-4-methoxystyrene

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Sodium amide (39 g) was dispersed in dry tetrahydrofuran (800 mls). Methyltriphenylphosphonium bromide (102 g) was added and the mixture stirred at R.T. for 2 hours. 3-allyloxy-4-methoxy-benzaldehyde (50 g) was then added dropwise over ca. 15 mins. and the mixture stirred for a further 3 hours. The mixture was filtered and the solvent removed from the filtrate under reduced pressure. The residue was washed with diethyl ether (1.51) and the solvent removed to yield a brown coloured resin. The washing process was repeated and the residue obtained was distilled under reduced pressure to give 3-allyloxy-4-methoxystyrene (29.5 g), b.p. 98°-104° C. at 0.8 mbar.

Workup

  1. stirringand the mixture stirred for a further 3 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent removed from the filtrate under reduced pressure
  4. washThe residue was washed with diethyl ether (1.51)
  5. customthe solvent removed
  6. customto yield a brown coloured resin
  7. customthe residue obtained
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-26d2155a0ac94079a164b7eb4823f55f
Source dataset
uspto-grants-1987_02
Patent number
US04640849

Reaction notes

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