Water → Ethofumesate-2-keto

HRID 67254Notes

Reaction equation

HRID 67254 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([OH:14])[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1)(=[O:4])=[O:3].O>C(O)(=O)C>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12](=[O:14])[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 962WaterHCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

Product 1

HCID 590774Ethofumesate-2-ketoYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-hydroxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (20 parts) in warm acetic acid (200 parts) was treated with 200 parts of a 20% aqueous solution of chromic oxide. After about 15 seconds the mixture was poured into water and the solution extracted with ether. The extracts were thoroughly washed with aqueous sodium bicarbonate, then dried and the solvent evaporated to give 2-oxo-2,3-dihydro-3,3-dimethyl-benzofuran-5-yl methanesulphonate (14 parts, 70% yield), melting point 120°-121° C. after recrystallisation from benzene-petroleum.

Workup

  1. extractionthe solution extracted with ether
  2. washThe extracts were thoroughly washed with aqueous sodium bicarbonate
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-4c5d7a7a90f74fb5ad3a32411a3549e5
Source dataset
uspto-grants-1982_08
Patent number
US04345932

Reaction notes

Loading…