3,5-Dimethoxybenzaldehyde → 4-(3,5-Dimethoxyphenyl)-3-butenoic acid

HRID 63636

Reaction equation

HRID 63636 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:43]=[C:44]([O:46][CH3:47])[CH:45]=1)[CH:41]=O>C1COCC1>[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:41]=[CH:6][CH2:5][C:2]([OH:4])=[O:3])[CH:43]=[C:44]([O:46][CH3:47])[CH:45]=1

Participants

5

Reactant 3

HCID 817473,5-DimethoxybenzaldehydeHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2733850(2-Carboxyethyl)triphenylphosphonium bromide

Product 1

HCID 851672434-(3,5-Dimethoxyphenyl)-3-butenoic acidYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (2-carboxyethyl)triphenylphosphonium bromide (13.7 g, 33 mmol) in dry THF (50 mL) was added NaHMDS (33 mL, 66 mmol) dropwise at −20° C. under N2 and the reaction stirred for 20 min. The reaction was cooled to −78° C. and 3,5-dimethoxybenzaldehyde (5.0 g, 30 mmol) was added, and the reaction mixture stirred overnight while warming to rt. The reaction was quenched with water and extracted with EtOAc. The aqueous layer was acidified to pH=2 with dilute HCl solution and extracted with EtOAc again. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give 2.54 g (38%) of the title compound as an orange gum. [M+H] Calc'd for C12H14O4, 223. Found, 223.

Workup

  1. stirringthe reaction mixture stirred overnight
  2. temperaturewhile warming to rt
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc
  5. extractionextracted with EtOAc again
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-334776fc2f144f408530c1cfa022325e
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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