Methyl 6-aminohexanoate → Caprolactam acetylene

HRID 35727

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O>C1(C)C=C(C)C=C(C)C=1>[C:7]1(=[O:9])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:2]#[CH:3]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 37.1 g (0.256 mol) of methyl 6-aminocaproate in 723 g of mesitylene is stirred under reflux at 140° C./500 bar for 12 h. Evaporating off the mesitylene under reduced pressure leaves 46.4 g of a caprolactam-acetylene mixture which, according to HPLC, contains 58.2% of caprolactam, which corresponds to 27.0 g (0.239 mol) and a yield of 93.4%.

Workup

customEvaporating off the mesitylene under reduced pressure

Sources & evidence

ORD record: ord-955be329f2be48739f9d648bd81f7872
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04767857

Linked notes

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