Acetic Anhydride → HCID 67954994, compound

HRID 1619176Notes

Reaction equation

HRID 1619176 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1/[C:19](=[CH:24]\[O:25][CH3:26])/[C:20]([O:22][CH3:23])=[O:21].[OH-].[Na+]>O>[C:1]([C:29]1[C:28]([CH3:31])=[CH:27][C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[C:19](=[CH:24]\[O:25][CH3:26])/[C:20]([O:22][CH3:23])=[O:21])=[C:9]([CH3:8])[CH:30]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 11631236(E)-2-(2-((2,5-dimethyl phenoxy)methyl phenyl))-3-methoxy acrylic acid methyl ester

Product 1

HCID 67954994HCID 67954994, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride (26 mL, 5 eq) was stirred together with methane sulfonyl (18 mL, 5 eq) at room temperature for 30 min and then combined with 18.0 g (55.16 mmol) of (E)-methyl 2-(2-((2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in step 1 at room temperature for an additional one hour. After completion of the reaction, the reaction mixture was dropwise added to water (500 mL), adjusted to pH 7 with 25%-NaOH and extracted twice with 250 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and filtered after which the solvent was removed by concentration in a vacuum. Crystallization in 100 mL of isopropyl ether (IPE) afforded 16.5 g of (E)-methyl 2-(2-((4-acetyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate in 81% yield as an ivory solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted twice with 250 mL of dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered after which the solvent
  5. customwas removed by concentration in a vacuum
  6. customCrystallization in 100 mL of isopropyl ether (IPE)

Sources & evidence

ORD record
ord-4001c831d74f430ca71c36828e542bb6
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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