Acetic Acid → Methyl 3-(3,5-dimethoxyphenyl)-2-(4-isopropyloxyphenyl)-3-oxopropionate

HRID 424030

Reaction equation

HRID 424030 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[C:8]([O:10]C)=O.[CH:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1)([CH3:19])[CH3:18].C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:16][O:15][C:13]1[CH:12]=[C:7]([C:8](=[O:10])[CH:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH:17]([CH3:19])[CH3:18])=[CH:22][CH:23]=2)[C:28]([O:30][CH3:31])=[O:29])[CH:6]=[C:5]([O:4][CH3:3])[CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 75074Methyl 3,5-DimethoxybenzoateHCID 525538Methyl 2-(4-isopropoxyphenyl)acetate

Product 1

HCID 66674372Methyl 3-(3,5-dimethoxyphenyl)-2-(4-isopropyloxyphenyl)-3-oxopropionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent4×

Conditions

Temperature
2.5 °C

Procedure

14.4 g of 60% sodium hydride in mineral oil (0.36 mol) which are washed with 2 times 50 ml of toluene are introduced into a three-necked round-bottomed flask. 90 ml of toluene and 28.3 g of methyl 3,5-dimethoxybenzoate (0.144 mol) are then introduced. The mixture is brought to reflux and a solution of 30 g of methyl p-isopropyloxyphenylacetate (0.144 mol) dissolved in 95 ml of toluene is added over 10 h. The mixture is maintained at reflux for 2 h. It is cooled to a temperature of 0-5° C. and a solution of glacial acetic acid (22.5 g, i.e. 0.374 mol) in 25 ml of toluene is added slowly. Then, at ambient temperature, 135 ml of water are added slowly.

Workup

  1. additionare introduced into a three-necked round-bottomed flask
  2. temperatureto reflux
  3. additionis added over 10 h
  4. temperatureThe mixture is maintained
  5. temperatureat reflux for 2 h

Sources & evidence

ORD record
ord-f134aec402f947f3b6994412ef96e865
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Linked notes

Loading…