Tributylamine → 1-(2-Ethylbutyl)cyclohexanecarbonyl chloride

HRID 1012371Notes

Reaction equation

[CH2:1]([CH:3]([CH2:14][CH3:15])[CH2:4][C:5]1([C:11](O)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:2].C(N(CCCC)CCCC)CCC.S(Cl)([Cl:31])=O.C(C(CC)CC1(C(OC(C2(CC(CC)CC)CCCCC2)=O)=O)CCCCC1)C>CCCCCCC>[CH2:1]([CH:3]([CH2:14][CH3:15])[CH2:4][C:5]1([C:11]([Cl:31])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6.0 kg (28.3 mol) 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid and 20.6 mL tributylamine (0.085 mmol) in 10 L heptane was warmed to 50° C. 2.5 L (34.5 mol) of thionyl chloride was added during 40 minutes at a temperature of 40-50° C. (reaction is endothermic, vigorous gas evolution) and the reaction mixture was kept at 53-55° C. An IPC-control after 60 minutes indicated complete conversion (0.04% 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid and no 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid anhydride). After removing volatile components under reduced pressure (70° C. bath, 13-8 mbar) 6.86 kg of the residue was obtained (assay 92.5% 1-(2-ethyl-butyl)-cyclohexanecarbonyl chloride, yield 97.2%)

Workup

customwas kept at 53-55° C
customAfter removing volatile components under reduced pressure (70° C. bath, 13-8 mbar) 6.86 kg of the residue

Sources & evidence

ORD record: ord-f29c107bb3724170b2098ec812571004
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977509B2

Reaction notes

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