Hexamethylphosphoramide → cis-5-(11-Tetradecenyloxy)furancarboxylic acid

HRID 649225

Reaction equation

HRID 649225 reaction equation
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14].[OH-].[Na+].Cl[C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1.CN(C)P(=O)(N(C)C)N(C)C>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:1]([O:15][C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 2348535-Chlorofuran-2-carboxylic acidHCID 1712010Cis-11-tetradecenol

Product 1

HCID 13655994cis-5-(11-Tetradecenyloxy)furancarboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

8.8 g (0.0414 mole) of cis-11-tetradecen-1-ol was combined with 4.0 g (0.0829 mole) of sodium hydroxide (50% in oil) in 200 ml of dry toluene and heated to reflux with stirring for 3 hours. 6.1 g (0.414 mole) of 5-chloro-2-furoic acid was added, followed by 25 ml of hexamethylphosphoric triamide (HMPA), and the reaction mixture refluxed with stirring for 20 hours, cooled, and acidified with acetic acid. The mixture was extracted into ether and the organic layer washed with water and with brine and evaporated to yield cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid, M.P. 89°-90° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturethe reaction mixture refluxed
  4. stirringwith stirring for 20 hours
  5. temperaturecooled
  6. extractionThe mixture was extracted into ether
  7. washthe organic layer washed with water and with brine
  8. customevaporated

Sources & evidence

ORD record
ord-0279fa8d7ede46d0841dfd25491599dc
Source dataset
uspto-grants-1988_04
Patent number
US04738984

Linked notes

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