Methanol → 3-Thienylglyoxylic acid

HRID 1707172Notes

Reaction equation

HRID 1707172 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:12])[C:7]([O:9]CC)=[O:8])=[CH:2]1.[OH-].[Na+].CO>O>[S:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:12])[C:7]([OH:9])=[O:8])=[CH:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12723741Ethyl oxo(thiophen-3-yl)acetate

Product 1

HCID 17136523-Thienylglyoxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl thien-3-yl-glyoxylate (10 g) and 2 N-sodium hydroxide (50 ml) was added sufficient methanol to produce a homogeneous solution, and the reaction was allowed to stand at room temperature for one hour. The solution was poured into water, extracted with ether, acidified with 2 N-hydrochloric acid and extracted with ether. The combined extracts were dried and evaporated to give an oil which was triturated with benzene-petroleum ether, and the resulting solid filtered and dried (7.5 g; 88%), m.p. 63°, νmax. (Nujol) 3600 and 1702 cm-1 (CO2H), τ (DMSO-d6) values include 1.29, 2.21, 2.38 (thien-3-yl protons).

Workup

  1. customto produce a homogeneous solution
  2. extractionextracted with ether
  3. extractionextracted with ether
  4. customThe combined extracts were dried
  5. customevaporated
  6. customto give an oil which
  7. customwas triturated with benzene-petroleum ether
  8. filtrationthe resulting solid filtered
  9. customdried (7.5 g; 88%), m.p. 63°, νmax

Sources & evidence

ORD record
ord-a676249f34a84418bdbae1124e6573d5
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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