Lauric Acid → HCID 12851997, compound

HRID 1156258Notes

Reaction equation

HRID 1156258 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].FC(F)(F)[C:17]([O:19][C:20](=O)[C:21](F)(F)F)=[O:18].C(OC(=O)[C:32]([C:34]1[O:35][CH:36]=[CH:37][CH:38]=1)=[CH2:33])C.Cl(O)(=O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>CCOCC>[O:14]=[C:1]([C:36]1[O:35][C:34](/[CH:32]=[CH:33]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:38][CH:37]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 5

HCID 3893Lauric AcidHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 24247Perchloric AcidHCID 22498573HCID 22498573, compound

Product 1

HCID 12851997HCID 12851997, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 11.8 g (0.0589 mole) of lauric acid and 14.8 g (0.0707 mole) of trifluoroacetic anhydride is stirred at room temperature for 1/2 hour. To the mixture 10.0 g (0.060 mole) of ethyl-2-furanylacrylate is added and the mixture is cooled to about -10° C. One ml of 70% perchloric acid is added and the mixture is warmed to room temperature and stirred for 1 hour. The mixture is diluted with 100 ml of ether and treated with saturated aqueous Na2CO3 until basic. The layers are separated and the ether layer washed with saturated aqueous Na2CO3, water, brine and then evaporated to dryness. The residue is distilled 160°-190° C. (0.1 mm Hg) to give ethyl (E)-3-[5-(1-oxododecyl)-2-furanyl]-2-propenoate, mp 50°-51° C.

Workup

  1. temperaturethe mixture is cooled to about -10° C
  2. temperaturethe mixture is warmed to room temperature
  3. stirringstirred for 1 hour
  4. customThe layers are separated
  5. washthe ether layer washed with saturated aqueous Na2CO3, water, brine
  6. customevaporated to dryness
  7. distillationThe residue is distilled 160°-190° C. (0.1 mm Hg)

Sources & evidence

ORD record
ord-3b6767ab7769439bb6474b567b8db8d3
Source dataset
uspto-grants-1982_06
Patent number
US04335098

Reaction notes

Loading…