1-Butanol → HCID 22921473, compound

HRID 2258421Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][CH3:14])[C:11]#[N:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)CCC.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:11]([C:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH2:13][CH3:14])[CH2:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])#[N:12]

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of 2-(4-nitrophenyl)butyronitrile (10.0 g), butanol (10 ml) and methyl acrylate (5.2 ml) was cooled to 10° C. in a 100 ml 3-necked round-bottomed flask, equipped with a magnetic follower. A solution of potassium tert-butoxide (0.6 g) in tert-butanol (10 ml) was added dropwise, maintaining the temperature at approximately 10° C. (solution turns purple). After addition was complete, the mixture was allowed to reach ambient temperature and then stirred for a further 2 hours. The reaction was worked-up by partitioning between diethyl ether (400 ml) and 1M KH2PO4 (400 ml). The ether layer was washed with water (50 ml), dried (MgSO4) and concentrated under reduced pressure to yield methyl 4-cyano-4-(4-nitrophenyl)hexanoate (14.1 g, 99%) as an orange oil.

Workup

customequipped with a magnetic follower
temperaturemaintaining the temperature at approximately 10° C. (solution turns purple)
additionAfter addition
customto reach ambient temperature
customby partitioning between diethyl ether (400 ml) and 1M KH2PO4 (400 ml)
washThe ether layer was washed with water (50 ml)
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c869719ccaeb4daf8e83a329b4bc0e2a
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661014

Reaction notes

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