Methyl phenoxyacetate → Methyl 4-[3-chloropropanoyl]phenoxyacetate

HRID 1290466Notes

Reaction equation

HRID 1290466 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>ClCCl>[Cl:17][CH2:18][CH2:19][C:20]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:8]=1)=[O:21]

Participants

5

Reactant 3

HCID 16365Methyl phenoxyacetateHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18918540Methyl 4-[3-chloropropanoyl]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (33.35 g) was added portionwise to a stirred cooled (<0° C.) solution of methyl phenoxyacetate (14.46 ml) and 3-chloroproponyl chloride (9.55 ml) in dichloromethane (500 ml). After the addition the ice-bath was removed and the mixture stirred for 1 hour when it was poured into ice-water (500 ml). The organic phase was separated and the aqueous portion extracted two times with dichloromethane. The combined dichloromethane extracts were washed with water, then brine and dried (MgSO4). The residue, after removal of the solvent in vacuo and trituration with ether gave methyl 4-[3-chloropropanoyl]phenoxyacetate, 22.3 g, as a solid: m.p. 89°-90° C.; NMR (d6DMSO) δ 7.95(2H,d), 7.05(2H,d), 4.92(2H,s), 3.91(2H,t), 3.71(3H,s), 3.49(2H,t); m/e 257(M+H)+ ; calculated for C12H13 ClO4 : C, 56.1; H, 5.0. found: C, 55.8; H, 5.1%.

Workup

  1. customwas removed
  2. additionwas poured into ice-water (500 ml)
  3. customThe organic phase was separated
  4. extractionthe aqueous portion extracted two times with dichloromethane
  5. washThe combined dichloromethane extracts were washed with water
  6. dry with materialbrine and dried (MgSO4)
  7. customThe residue, after removal of the solvent in vacuo and trituration with ether

Sources & evidence

ORD record
ord-5753f9a3cb4747b8a1b7e982a6e4d239
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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