Methyl Acetate → HCID 59504314, compound

HRID 418917Notes

Reaction equation

HRID 418917 reaction equation
C[O-].[Na+].C(OC)(=O)C.[CH3:9][O:10][C:11](=[O:29])[CH:12]=[C:13]1[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][CH:14]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1>CS(C)=O.C(OCC)(=O)C>[CH3:9][O:10][C:11](=[O:29])[CH2:12][C:13]1[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][C:14]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1

Participants

6

Reactant 3

HCID 6584Methyl AcetateHCID 10942334Sodium MethoxideHCID 66651947HCID 66651947, compound

Product 1

HCID 59504314HCID 59504314, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve sodium methoxide (0.99 g, 18.4 mmol) in DMSO (37 ml) add methyl acetate (1 ml), add [2-(3-methoxy-phenyl)-4,4-dimethyl-cyclohexylidene]-acetic acid methyl ester (5.3 g, 18 mmol). Heat at 100° C. stirring over night. Dilute with ethyl acetate (50 ml), wash with brine 4× (30 ml), dry, and concentrate to give the title compound (5.2 g 98%): 1H NMR (CDCl3) δ 7.24-7.18 (m, 1H), 6.78-6.68 (m, 3H), 3.79 (s, 3H), 3.65 (s, 2H), 3.59 (s,1H), 2.95 (s,1H), 2.15-2.07 (m, 3H), 1.55(s, 3H), 1.49-1.46 (m,1H), 0.98 (s, 6H).

Workup

  1. washwash with brine 4× (30 ml)
  2. customdry
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-ffb1b0cb7d7d4690a8f7811c56090269
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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