Acetic Anhydride → HCID 136341639, compound

HRID 1908383Notes

Reaction equation

HRID 1908383 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15](=[N:17][OH:18])[CH3:16])[CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:19][C:20](OC(C)=O)=[O:21]>>[C:20]([O:18]/[N:17]=[C:15](/[C:10]1[CH:9]=[C:8]([C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:6]2)[CH:13]=[CH:12][C:11]=1[OH:14])\[CH3:16])(=[O:21])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136341637HCID 136341637, compound

Product 1

HCID 136341639HCID 136341639, compoundYield 99%

Procedure

The solution of 1-[4-hydroxy-3-(1-hydroxyimino-ethyl)-phenyl]-cyclopropanecarboxylic methyl ester (10.0 g, 40.1 mmol) in Ac2O (250 mL) was heated at 45° C. for 4 h. The Ac2O was removed by evaporation under vacuum before water (100 mL) and EtOAc (100 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×2). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give (E)-methyl 1-(3-(1-(acetoxyimino)ethyl)-4-hydroxyphenyl)cyclopropanecarboxylate (10.5 g, 99%), which was used in the next step without further purification.

Workup

  1. customThe Ac2O was removed by evaporation under vacuum before water (100 mL) and EtOAc (100 mL)
  2. additionwere added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (100 mL×2)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-0c47c1ad13c14e749cc977918dda914f
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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