Trifluoroacetic acid → Trifluoroacetic acid--azonan-2-one (1/1)

HRID 1353133Notes

Reaction equation

HRID 1353133 reaction equation
[C:1]1(=[O:10])[NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:11][C:12]([F:17])([F:16])[C:13]([OH:15])=[O:14]>C1C=CC=CC=1>[F:11][C:12]([F:17])([F:16])[C:13]([OH:15])=[O:14].[C:1]1(=[O:10])[NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13632Octahydro-2H-azonin-2-one

Product 1

HCID 71405229Trifluoroacetic acid--azonan-2-one (1/1)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a 100 ml flask containing 14.12 g of octanolactam (0.1 mol), 30 ml benzene was added and stirred for dissolution. 11.40 g of trifluoroacetic acid (0.1 mol) was added dropwise into the flask over 30 min at room temperature. Then the reaction was stirred for another 4 hours. Desired product was formed after benzene was removed under reduced pressure and dried at 110° C. under 1–5 mmHg for 1 hour. The colorless, slightly viscous, moisture- and water-stable liquid of octanolactam trifluoroacetate was obtained with a yield of 98.2%, which has a glass transition temperature of −64° C., a density of 1.27 g/ml, a viscosity of 62 cP, an electrochemical window of 2.1 V, an ionic conductivity of 2.57×10−4 S/cm, and a Hammett acidic scale H0 of 4.79 using methyl yellow as indicator. No melting point was observed.

Workup

  1. additionwas added
  2. stirringThen the reaction was stirred for another 4 hours

Sources & evidence

ORD record
ord-b9598c9abde848fea809197cea0f8eb6
Source dataset
uspto-grants-2007_05
Patent number
US07220869B2

Reaction notes

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