Water → HCID 22039648, compound

HRID 1016783Notes

Reaction equation

HRID 1016783 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=O)[CH:6]=[C:7]([CH:9]=[O:10])[CH:8]=1.[C:13]([O-])([O-])=O.[K+].[K+].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[C:5]([CH:11]=[CH2:13])[CH:4]=1)[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 108882575-methoxyisophthalaldehyde

Product 1

HCID 22039648HCID 22039648, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the 5-methoxy-benzene-1,3-dicarbaldehyde (3.68 g, 22.4 mmol) obtained in Example 198.1, methyl-triphenylphosphonium bromide (8.17 g, 22.4 mmol), K2CO3 (3.10 g, 22.4 mmol), water (0.68 ml) and dioxan (51 ml) was heated for 2 h. to 90° C. The reaction mixture was concentrated and the product was purified by chromatography (SiO2, hexane/CH2Cl2 4:1). There were obtained 1.74 g (48%) of 3-methoxy-5-vinyl-benzaldehyde as a colorless oil; MS: 162 ([M]+).

Workup

  1. temperaturewas heated for 2 h. to 90° C
  2. concentrationThe reaction mixture was concentrated
  3. customthe product was purified by chromatography (SiO2, hexane/CH2Cl2 4:1)

Sources & evidence

ORD record
ord-6a5ddfa27f8e45b5a519d76208296e5c
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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