Water → Ethofumesate-2-keto

HRID 2072313Notes

Reaction equation

HRID 2072313 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-e73e3343abfb424f95f5c9b48d304363
Source dataset
uspto-grants-1977_09
Patent number
US04051154

Reaction notes

Loading…