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

HRID 266724

反応式

HRID 266724 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 18918540Methyl 4-[3-chloropropanoyl]phenoxyacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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) 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 C12H13ClO4 : C, 56.1; H, 5.0. found: C, 55.8; H, 5.1%.

後処理

  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

出典と根拠

ORDレコード
ord-400178a381d048cda40bca726d32b8c4
出典データセット
uspto-grants-1997_07
特許番号
US05652242

関連ノート

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