Trifluoroacetic anhydride → HCID 54574519, compound

HRID 1156260Notes

Reaction equation

[CH3:1][CH:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:3][C:4]([OH:6])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=[C:37]([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[Na+].[Na+]>Cl(O)(=O)(=O)=O.CCOCC>[CH3:43][C:37](=[CH:36][C:32]1[O:31][C:35]([C:4](=[O:6])[CH2:3][CH:2]([CH3:1])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:34][CH:33]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 24.2 g (0.1 mole) of 3,7,11-trimethyldodecanoic acid and 21.0 g (0.1 mole) of trifluoroacetic anhydride is stirred at reflux for 1/2 hour. The mixture is cooled and 18.0 g (0.1 mole) of ethyl 3-(2-furanyl)-2-methylpropenoate is added. The mixture is cooled to about 0° C. and 5 drops of 70% perchloric acid is added. The mixture is stirred at 0° C. for 2 hours, then diluted with anhydrous ether and treated with saturated aqueous sodium carbonate solution until basic. The layers are separated and the ether layer washed with water, brine and evaporated to dryness. The residue is distilled at reduced pressure to give ethyl 2-methyl-3-[5-(1-oxo-3,-7,11-trimethyldodecyl)-2-furanyl]-2-propenoate.

Workup

temperatureat reflux for 1/2 hour
temperatureThe mixture is cooled
stirringThe mixture is stirred at 0° C. for 2 hours
customThe layers are separated
washthe ether layer washed with water, brine
customevaporated to dryness
distillationThe residue is distilled at reduced pressure

Sources & evidence

ORD record: ord-50551235ea1c42aead934b1e34fdabc7
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04335098

Reaction notes

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