Sodium Carbonate → 4-Methyl-3-formyl-pent-3-en-1-oic acid

HRID 637526Notes

Reaction equation

HRID 637526 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[I-].C[O:9][CH:10]1[O:14][C:13](=[O:15])[CH2:12][CH:11]1[C:16]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:18])[CH3:17]>O.CO>[CH:10]([C:11](=[C:16]([CH3:18])[CH3:17])[CH2:12][C:13]([OH:15])=[O:14])=[O:9]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 20257036[1-(5-methoxy-2-oxo-4,5-dihydro-3H-furan-4-yl)-1-methyl-1-ethyl]-triphenylphosphonium iodide

Product 1

HCID 128824154-Methyl-3-formyl-pent-3-en-1-oic acidYield 52.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 0.700 g of sodium carbonate in 8 ml of water was added to a solution of 0.700 g of the product of Step A in 1 ml of methanol and the mixture was stirred for 2 hours at 20° C. and was filtered. The filtrate was adjusted to a pH of 2 and was saturated with sodium chloride. The mixture was extracted with chloroform and the organic phase was evaporated to dryness. The residue was crystallized from isopropyl ether to obtain 0.095 g of 3-formyl-4-methyl-pent-3-ene-1-oic acid melting at 102° C.

Workup

  1. filtrationwas filtered
  2. extractionThe mixture was extracted with chloroform
  3. customthe organic phase was evaporated to dryness
  4. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-43bd5704008745cbb4a4de698f4be5fd
Source dataset
uspto-grants-1985_12
Patent number
US04556732

Reaction notes

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