Hydroxyphenylacetic acid → HCID 8671781, compound

HRID 1761966Notes

Reaction equation

HRID 1761966 reaction equation
[K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.CN(C)P(N(C)C)(N(C)C)=O.Cl[CH2:25][C:26]([NH2:28])=[O:27]>CS(C)=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:25][C:26](=[O:27])[NH2:28])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 6580ChloroacetamideHCID 12679HexamethylphosphoramideHCID 5462222Potassium

Product 1

HCID 8671781HCID 8671781, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The potassium salt of 4-hydroxyphenylacetic acid (9.5 g, 0.1 mol) was taken up in a mixture of dimethylsulfoxide (80 mL) and hexamethylphosphoramide (5.37 g, 0.1 mol). 2-Chloroacetamide (13.5 g, 0.3 mol) was added and the reaction mixture was first stirred at room temperature for 24 hours, then heated for 1 hour. The reaction mixture was evaporated, then cooled. The product which separated was taken up in ethyl acetate (150 mL), stirred, filtered and evaporated. The oily residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and evaporated to give the desired ester, carbamoylmethyl 4-hydroxyphenylacetate, melting at 85°-87° C., in 48.8% yield.

Workup

  1. temperatureheated for 1 hour
  2. customThe reaction mixture was evaporated
  3. temperaturecooled
  4. customThe product which separated
  5. stirringstirred
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  9. customThe organic layer was separated
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-61082e50beac466cb00636920991c559
Source dataset
uspto-grants-1989_05
Patent number
US04829086

Reaction notes

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