Toluene → Diethyl-2-(2'-methyl-4-chloro-phenoxy)-propionyl-malonate

HRID 247531Notes

Reaction equation

HRID 247531 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:10]=1[O:11][CH:12]([CH3:16])[C:13]([OH:15])=O.C([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C.[C:37]([O:45][CH2:46][CH3:47])(=[O:44])[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CCOCC.C(N(CC)CC)C>[CH2:42]([O:41][C:39](=[O:40])[CH:38]([C:13](=[O:15])[CH:12]([O:11][C:10]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:9]=1[CH3:8])[CH3:16])[C:37]([O:45][CH2:46][CH3:47])=[O:44])[CH3:43]

Participants

6

Reactant 3

HCID 1140TolueneHCID 7153MecopropHCID 7761Diethyl Malonate

Product 1

HCID 20159510Diethyl-2-(2'-methyl-4-chloro-phenoxy)-propionyl-malonateYield 88.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Into a 200 ml round-bottomed flask equipped with a magnetic stirrer, a thermometer, a dropping funnel and a calcium chloride tube 100 ml of toluene, 10.1 g of triethyl amine and 21 g of 2-(2'-methyl-4'-chloro-phenoxy)-propionic acid are weighed in. The reaction mixture is cooled under 0° C. and 10.8 g of ethyl chloro formiate are added dropwise at such a rate that the temperature should be between -1° C. and 0° C. The thick suspension formed is stirred for a further period of 20 minutes, whereupon a mixture of diethyl-ethoxy-magnesium-malonate prepared from 17.6 g of diethyl malonate and 50 ml ether is added dropwise at such a rate that the temperature should not exceed 0° C. The reaction mixture is allowed to stand at room temperature for 16 hours and worked up as described in Example 1. Thus 31 g of the desired compound are obtained in the form of a pale yellow oil, yield 88%, nD25 =1.348.

Workup

  1. customInto a 200 ml round-bottomed flask equipped with a magnetic stirrer
  2. addition10.8 g of ethyl chloro formiate are added dropwise at such a rate that the temperature
  3. customshould be between -1° C. and 0° C
  4. customThe thick suspension formed
  5. additionis added dropwise at such a rate that the temperature should not
  6. customexceed 0° C

Sources & evidence

ORD record
ord-c19771cd27164a46927df8c771e26fd4
Source dataset
uspto-grants-1987_11
Patent number
US04708733

Reaction notes

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