Hydrochloric Acid → 3-(2-oxocyclododecyl)propanoic acid

HRID 1415437Notes

Reaction equation

HRID 1415437 reaction equation
[C:1]([CH:6]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:18])(OCC)=O.[H-].[Na+].[C:21]1(=[O:25])[O:24]C[CH2:22]1.[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[O:18]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:6]1[CH2:1][CH2:22][C:21]([OH:25])=[O:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2365Beta-PropiolactoneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 4463978Cyclododecanecarboxylic acid, 2-oxo-, ethyl ester

Product 1

HCID 27750833-(2-oxocyclododecyl)propanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Cyclododecanone and diethyl carbonate were allowed to react in the presence of a base to give 2-carboethoxycyclododecanone in 93% yield. Ten grams of the 2-carboethoxycyclododecanone was dissolved in 40 ml of toluene and the resulting solution was added dropwise into a solution of 2.4 g of sodium hydride (purity 60%) suspended in toluene and kept at 80° C. After the completion of the dropping, the solution thus obtained was stirred for 30 minutes and then the reaction temperature was cooled to room temperature. Thereafter, into the solution was dropped 5.7 g of β-propiolactone and further 25 ml of aqueous sodium hydroxide solution was added, and was refluxed for 4 hours. After the reaction was complete, the aqueous layer of the solution was drawn off and acidified with hydrochloric acid to give 8.5 g of β-(2-oxocyclododecyl)propionic acid as white crystals. The product melts at 101° to 102° C.

Workup

  1. customkept at 80° C
  2. customAfter the completion of the dropping, the solution thus obtained
  3. additionwas added
  4. temperaturewas refluxed for 4 hours

Sources & evidence

ORD record
ord-721a944399fd4ced84abd0bc423d6bf4
Source dataset
uspto-grants-1977_01
Patent number
US04005107

Reaction notes

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