Acetic Acid → HCID 54506149, compound

HRID 280610Notes

Reaction equation

HRID 280610 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:6]=2[C:7]=1[CH3:8].[N+](=[CH2:18])=[N-].C(O)(=O)C>CO>[CH3:18][O:14][C:13]([C:10]1[CH:11]=[CH:12][C:5]2[O:4][C:3]([CH2:2][OH:1])=[C:7]([CH3:8])[C:6]=2[CH:9]=1)=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550Diazomethane2×HCID 23320901HCID 23320901, compound

Product 1

HCID 54506149HCID 54506149, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-hydroxymethyl-3-methylbenzofuran-5-carboxylic acid (0.69 g) in methanol (250 ml) was treated with an excess of an ethereal solution of diazomethane. The solution was allowed to stand for 11/2 hours at 0° and then the excess of diazomethane was decomposed by dropwise addition of acetic acid until no further effervescence was apparent. The solution was evaporated and the residue was dissolved in ether. The solution was washed with sodium bicarbonate, dried (Na2SO4) and evaporated to give a quantitative yield of 2-hydroxymethyl-3-methylbenzofuran-5-carboxylic acid methyl ester, m.p. 96°-98° (from ethyl acetate/petrol).

Workup

  1. custom2 hours
  2. customat 0°
  3. customThe solution was evaporated
  4. dissolutionthe residue was dissolved in ether
  5. washThe solution was washed with sodium bicarbonate
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-e0494ad6b4fc465d8f0e6a90c2a35ed8
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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