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

HRID 864770Notes

Reaction equation

HRID 864770 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-chloropropionyl 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) δ7.95(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 C12H13ClO4 : 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-7071a3b4bf9842159cf131346402bf29
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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