Methanol → Cyclohexyl 5-cyanopentanoate

HRID 1439538Notes

Reaction equation

[C:1](#[N:6])[CH2:2][CH:3]=[CH:4][CH3:5].[CH:7]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:14][OH:15]>>[CH:7]1([O:13][C:14](=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]#[N:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Reactant 3

HCID 887Methanol

HCID 7966Cyclohexanol

HCID 207503-Pentenenitrile, Pract.

Product 1

HCID 54021572Cyclohexyl 5-cyanopentanoateYield 47.3%

Conditions

Temperature: 160 °C

Procedure

Example 3 is carried out with an equal amount of 3-pentenonitrile in place of 4-pentenonitrile, and with the methanol replaced by 25 parts of cyclohexanol, the mixture is heated to 160° C, and the autoclave is shaken for 4 hours, under a final pressure of 260 bars. 9.9 parts of 5-cyanovaleric acid cyclohexyl ester (47.3% of theory) of boiling point 124.5°-125.5° C/0.5 mm Hg, nD20 = 1.4598, are obtained.

Sources & evidence

ORD record: ord-f61d3112559649c79aacbb508e41e0c3
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04060543

Reaction notes

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