Tetrahydrofuran → 2-Methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate

HRID 1650394Notes

Reaction equation

HRID 1650394 reaction equation
C(O[C:5]([C:7]1[CH:15]=[CH:14][C:12]([OH:13])=[C:9]([O:10][CH3:11])[CH:8]=1)=O)(=O)C.[CH:16]([C:18]1C=CC=CC=1P(=C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17].C1C[O:41][CH2:40][CH2:39]1>>[C:40]([O:13][C:12]1[CH:14]=[CH:15][C:7]([CH:5]=[CH:18][CH:16]=[O:17])=[CH:8][C:9]=1[O:10][CH3:11])(=[O:41])[CH3:39]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 19764733HCID 19764733, compoundHCID 71307382HCID 71307382, compound

Product 1

HCID 30176002-Methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetateYield 54%

Procedure

Acetoxy vanillin (5.0 g, 2.6×10-2M) is dissolved in dry THF (300 ml) with formyl methylenetriphenylphosphorane (78 g, 2.6×10-2M) and refluxed under an atmosphere of argon for 80 hours. The reaction mixture is concentrated to dryness and chromatographed on flash silica to afford 4-acetoxy-3-methoxycinnamaldehyde (3 g, 54% yield); mp=83°-86° C.

Workup

  1. temperaturerefluxed under an atmosphere of argon for 80 hours
  2. concentrationThe reaction mixture is concentrated to dryness
  3. customchromatographed on flash silica

Sources & evidence

ORD record
ord-6b87d22d60474f1fb6c06aebdcd429f8
Source dataset
uspto-grants-1990_05
Patent number
US04924002

Reaction notes

Loading…