Iodoethane → Methyl 2-(p-chlorophenoxy)-2-[p-(p-chlorophenoxy)phenyl]butyrate

HRID 1863345Notes

Reaction equation

HRID 1863345 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.Cl[C:30]1C=CC(OC(C2C=CC(OC3C=CC(Cl)=CC=3)=CC=2)C(OC)=O)=CC=1.CN(C)P(N(C)C)(N(C)C)=O.C(I)C>O1CCCC1.O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)=[CH:15][CH:14]=2)([CH2:12][CH3:30])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 12679HexamethylphosphoramideHCID 12531843Methyl(p-chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetateHCID 12531902Methyl 2-(p-chlorophenoxy)-2-[p-(p-chlorophenoxy)phenyl]propionate

Product 1

HCID 20392631Methyl 2-(p-chlorophenoxy)-2-[p-(p-chlorophenoxy)phenyl]butyrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.015 mole of lithium N,N-diisopropylamide (prepared as in example 55) in tetrahydrofuran is chilled to -65° C. to -75° C. To the solution is added methyl (p-chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of tetrahydrofuran. To the mixture is added 5 ml of hexamethylphosphoramide and while chilling to -65° C. to -75° C., 4.68 g of ethyl iodide is added. After 1 hr., the mixture is allowed to warm to room temperature and stirr overnight. The mixture is poured into water and extracted with ether. The ether extracts are washed with 10% hydrochloric acid, water, saturated NaHCo3, saturated NaCl solution and dried (MgSO4). Evaporation of the solvent gives the product as an oil.

Workup

  1. temperaturewhile chilling to -65° C. to -75° C.
  2. extractionextracted with ether
  3. washThe ether extracts are washed with 10% hydrochloric acid, water, saturated NaHCo3, saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-17e1205b157a4a7d855937b538b226d9
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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