Water → HCID 19699056, compound

HRID 862997Notes

Reaction equation

HRID 862997 reaction equation
O=[C:2]1[C:7]2[C:8]([C:11]([OH:13])=[O:12])=[CH:9][O:10][C:6]=2[CH2:5][CH2:4][CH2:3]1.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+].O>C(O)C>[OH:16]/[N:15]=[C:2]1/[CH2:3][CH2:4][CH2:5][C:6]2[O:10][CH:9]=[C:8]([C:11]([OH:13])=[O:12])[C:7]/1=2

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 7139374-Oxo-4,5,6,7-tetrahydro-1-benzofuran-3-carboxylic acid

Product 1

HCID 19699056HCID 19699056, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 30.0 g of 4,5,6,7-tetrahydro-4-oxo-3-benzofurancarboxylic acid in 225 ml of ethanol is added 22.97 g of hydroxylamine hydrochloride, followed by 18.10 g of sodium acetate and 55 ml of water. The reaction mixture is heated at reflux for 2.5 hours and concentrated in vacuo to a residue which is diluted with 600 ml of ethyl acetate, washed with 2×200 ml of water, brine and dried over Na2SO4. The organic layer is concentrated in vacuo to a residue which is dried under vacuum to give 31.0 g of the desired product as a solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2.5 hours
  3. concentrationconcentrated in vacuo to a residue which
  4. additionis diluted with 600 ml of ethyl acetate
  5. washwashed with 2×200 ml of water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe organic layer is concentrated in vacuo to a residue which
  8. customis dried under vacuum

Sources & evidence

ORD record
ord-825d5a29600c4522ac7cf5dbb73ba94c
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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