Acetic Anhydride → 3-Acetoxy-4-hydroxy-benzoic acid ethyl ester

HRID 1918316Notes

Reaction equation

HRID 1918316 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)[CH3:2].[CH3:14][C:15]([O-:18])(C)C.[K+].C(OC(=O)C)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][C:15](=[O:18])[CH3:14])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 77547Ethyl 3,4-DihydroxybenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 671701733-Acetoxy-4-hydroxy-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dihydroxy-benzoic acid ethyl ester (550 mg, 3.02 mmol) was dissolved in DMF (5 ml), potassium tert-butylate (210 mg, 2.87 mmol) was added and the mixture stirred for 10 min. Acetic anhydride (339 mg, 3.32 mmol) was added and stirring continued for 10 min. The mixture was partitioned between EA and 2 N hydrochloric acid, the aqueous phase extracted with EA, the combined organic phases were dried over sodium chloride, decanted and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient) to yield the title compound.

Workup

  1. stirringstirring
  2. waitcontinued for 10 min
  3. customThe mixture was partitioned between EA and 2 N hydrochloric acid
  4. extractionthe aqueous phase extracted with EA
  5. dry with materialthe combined organic phases were dried over sodium chloride
  6. customdecanted
  7. customevaporated to dryness
  8. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-5b42078074f44b2d8aa89e855e971ecf
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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