Water → 4-Methyl-3-formyl-pent-3-en-1-oic acid

HRID 2166956Notes

Reaction equation

HRID 2166956 reaction equation
C1(C)C=CC(S([C:10]([C@H:13]2[C@H:17]([OH:18])[O:16][C:15](=[O:19])[CH2:14]2)([CH3:12])[CH3:11])(=O)=O)=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:17]([C:13](=[C:10]([CH3:12])[CH3:11])[CH2:14][C:15]([OH:19])=[O:16])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 12850319HCID 12850319, compound

Product 1

HCID 128824154-Methyl-3-formyl-pent-3-en-1-oic acidYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

0.788 g of the product of Step C was added to a solution of 20 ml of water and 2.4 ml of methanol and 0.790 g of sodium carbonate were added with stirring at -5° C. to the resulting mixture. The mixture was stirred at 20° C. for 2 hours and was extracted with ether. The aqueous phase was acidified to a pH of 3.5 by addition of 1 N aqueous hydrochloric acid. The mixture was extracted with chloroform and the organic phase was evaporated to dryness under reduced pressure to obtain 0.310 g of 3-formyl-4-methyl-pent-3-ene-1-oic acid melting at 102° C.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at 20° C. for 2 hours
  3. extractionwas extracted with ether
  4. additionThe aqueous phase was acidified to a pH of 3.5 by addition of 1 N aqueous hydrochloric acid
  5. extractionThe mixture was extracted with chloroform
  6. customthe organic phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-22fe47805ca249e99df181a8e97098c5
Source dataset
uspto-grants-1983_06
Patent number
US04390724

Reaction notes

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