Sodium Carbonate → HCID 15841978, compound

HRID 436522Notes

Reaction equation

HRID 436522 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8](=[O:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[O:17][CH:18]=[CH:19][CH:20]=1.[C:22](=O)([O-])[O-:23].[Na+].[Na+]>CN(C)C=O>[CH3:6][O:7][C:8](=[O:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[O:17][C:18]([CH:22]=[O:23])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 557175Methyl 8-(2-furyl)octanoate

Product 1

HCID 15841978HCID 15841978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.13 g of phosphorous oxychloride were added, while stirring, to 2.93 g of dimethyl formamide at 5°-10° C for 5 minutes. The mixture was kept at 0°-5° C for 40 minutes and then heated to room temperature. Immediately, and with vigorous stirring, 8.96 g of 8-(2-furyl)-octanoic acid methyl ester were added, whereupon the mixture was cooled to 5°-10° C in an ice-salt bath during 1 hour. After further 1 hour at room temperature, 40 g of ice were added, whereupon the mixture was neutralized with 10 g of sodium carbonate. The two phases were then separated, and the aqueous phase was extracted with ether. The combined organic phases were dried and then distilled. Boiling point 144° C at 0.2 mm Hg.

Workup

  1. temperaturewas cooled to 5°-10° C in an ice-salt bath during 1 hour
  2. waitAfter further 1 hour at room temperature
  3. customThe two phases were then separated
  4. extractionthe aqueous phase was extracted with ether
  5. customThe combined organic phases were dried
  6. distillationdistilled

Sources & evidence

ORD record
ord-16aa0f062e594790be7dc431eeea9cad
Source dataset
uspto-grants-1977_02
Patent number
US04009187

Reaction notes

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