Chloroacetic Acid → Chloroacetic acid--azepan-2-one (1/1)

HRID 1353128Notes

Reaction equation

HRID 1353128 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:9][CH2:10][C:11]([OH:13])=[O:12]>C1C=CC=CC=1>[Cl:9][CH2:10][C:11]([OH:13])=[O:12].[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 7768Caprolactam

Product 1

HCID 21102322Chloroacetic acid--azepan-2-one (1/1)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

To a 100 ml flask containing 11.32 g of ε-caprolactam (0.1 mol), 30 ml benzene was added and stirred for dissolution. Then 9.45 g of chloroacetic acid (0.1 mol) in 20 ml benzene was added dropwise into the flask over 20 min at room temperature. Then the reaction was stirred for another 7 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 yellowish, moisture- and water-stable liquid of caprolactam chloroacetate was obtained with a yield of 95.9%, which has an ionic conductivity of 2.9×10−5 S/cm, a glass transition temperature of −67° C., and a Hammett acidic scale H0 of 5.03 using methyl yellow as indicator. After several days, it changed into a yellowish solid with melting point of 29° C.

Workup

  1. additionwas added
  2. stirringThen the reaction was stirred for another 7 hours

Sources & evidence

ORD record
ord-8c3c66f6f21440fb84582ac24ec22c28
Source dataset
uspto-grants-2007_05
Patent number
US07220869B2

Reaction notes

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