1-(4-Cyclohexylphenyl)ethan-1-one → (E)-4-(4-cyclohexyl-phenyl)-3-pentene-2-one

HRID 1605663Notes

Reaction equation

HRID 1605663 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:18]/[C:19](/[CH3:26])=[CH:20]/C(OCC)=O)C>>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[CH3:14])=[CH:20]/[C:19](=[O:18])[CH3:26])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 877151-(4-Cyclohexylphenyl)ethan-1-oneHCID 5354173Ethyl (2E)-3-ethoxy-2-butenoate

Product 1

HCID 68134323(E)-4-(4-cyclohexyl-phenyl)-3-pentene-2-oneYield 55%

Procedure

(E)-4-(4-cyclohexyl-phenyl)-3-pentene-2-one was prepared analogous to Example 52 from 4'-cyclohexyl-acetophenone and ethyl (E)-3-ethoxy-crotonate with a yield of 55% of theory. B.p. 148°-151°C at 0.4 mm Hg; m.p. 49°-50°C (after recrystallization from methanol and petroleum ether). Characteristic signals in NMR (CDCl3): τ 3.50 (1H-q; /J/=1.2 ± 0.1 Hz); τ 7.50 (3H-d; /J/=1.2 ± 0.1 Hz).

Workup

  1. customm.p. 49°-50°C (after recrystallization from methanol and petroleum ether)

Sources & evidence

ORD record
ord-d3f022f3a80f4d779631c126fce9dc9c
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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