Sodium Bicarbonate → HCID 13093557, compound

HRID 1163940Notes

Reaction equation

HRID 1163940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]([O:14]C=O)[C:11]([NH2:13])=[O:12].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]([OH:14])[C:11]([NH2:13])=[O:12]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 13093556HCID 13093556, compound

Product 1

HCID 13093557HCID 13093557, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Chloro-6-methoxyphenyl)-2-formoxyacetamide (10 g.) was dissolved in 50 ml. of ethyl acetate by brief warming. The resulting solution was equilibrated with 30 ml. of saturated sodium bicarbonate by stirring for 30 minutes. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate, treated with activated carbon, filtered through a bed of diatomaceous earth and concentrated in vacuo to a foam. Trituration with hexane gave 2-(2-chloro-6-methoxyphenyl)-2-hydroxyacetamide [6.7 g., pnmr/CDCl3 /delta: 7.9 ppm peak gone, includes 2 doublets between 5.1 and 5.9 ppm (OH-CH splitting) which collapse to a singlet at 5.6 ppm (CH) on D2O exchange].

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. additiontreated with activated carbon
  4. filtrationfiltered through a bed of diatomaceous earth
  5. concentrationconcentrated in vacuo to a foam

Sources & evidence

ORD record
ord-4d2140a38824412b8a4ba003b919706f
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

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