Sodium Acetate → HCID 22628362, compound

HRID 278432Notes

Reaction equation

HRID 278432 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[OH:18])[CH:2]=[CH2:3].[CH3:19][C:20]([O-])=[O:21].[Na+]>C(OC(=O)C)(=O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:18][C:20](=[O:21])[CH3:19])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 18701949HCID 18701949, compound

Product 1

HCID 22628362HCID 22628362, compoundYield 650%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

2-Allyl-4-benzyloxy-phenol (2.87 g, 12 mmol) was taken up in acetic anhydride (40 ml) and NaOAc (150 mg, 1.8 mmol) was added and the mixture heated 18 hr at 80° C. After cooling, the reaction mixture was evaporated to afford an oil which was partitioned between EtOAc and H2O (100 ml) and the aqueous phase was extracted with EtOAc (100 ml) and the combined organic phases were dried with MgSO4, filtered and evaporated to afford acetic acid-2-allyl-4-benzyloxy-phenyl ester as a pale yellow oil (3.30 g, 11.7 mmol, 97%), MS: m/e=282.1 (M+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. customto afford an oil which
  4. customwas partitioned between EtOAc and H2O (100 ml)
  5. extractionthe aqueous phase was extracted with EtOAc (100 ml)
  6. dry with materialthe combined organic phases were dried with MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ccf186c7ffdf4382b87873298c0fa13c
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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