4-(4-methoxyphenyl)cyclohexanone synthesis
- Product Name:4-(4-methoxyphenyl)cyclohexanone
- CAS Number:5309-16-0
- Molecular formula:C13H16O2
- Molecular Weight:204.26
Yield:5309-16-0 100%
Reaction Conditions:
with potassium carbonate in lithium hydroxide monohydrate;propan-2-one;
Steps:
2 Preparation of Fmoc-1-amino-4-(4-methoxyphenyl)cyclohexane-1-carboxylic acid (Fmoc-4-MeOApc-OH)
EXAMPLE 2 Preparation of Fmoc-1-amino-4-(4-methoxyphenyl)cyclohexane-1-carboxylic acid (Fmoc-4-MeOApc-OH) A solution of 4-(4-hydroxyphenyl)cyclohexanone (5.0 g, 26.3 mmol) in acetone (100 mL) was treated with K2CO3 (14.5 g, 105 mmol, 4 equiv) and iodomethane (4.9 mL, 11.2 g, 78.6 mmol, 3 equiv.). The reaction was heated at 65° C. overnight. After the solvent was removed, the residue was treated with H2O and extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na2SO4 and concentrated in vacuum to give the spectroscopically pure 4-(4-methoxyphenyl)cyclohexanone (5.34 g, 100%). 1H-NMR(CDCl3) 7.16 (dt, 2H), 6.87 (dt, 2H), 3.78 (s, 3H), 2.99 (tt, 1H), 2.47-2.53 (m, 4H), 2.20 (m, 2H) and 1.83-1.98 (m, 2H); MS (electrospray) m/e, 205 (M+1)+, Calcd for C13H16O2, 204.
References:
US2001/56179,2001,A1
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