Methyl iodide → HCID 22114273, compound

HRID 565118Notes

Reaction equation

HRID 565118 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[OH:15])[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:16]I.[OH-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 12363402HCID 12363402, compound

Product 1

HCID 22114273HCID 22114273, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-hydroxyphenoxyacetate (1.5 g, 7.6 mmol) was reacted with SO2Cl2 (1.5 mL) to give ethyl 3-chloro-4-hydroxyphenoxyacetate (700 mg, ˜80% pure) as a white powder. To a solution of ethyl 3-chloro-4-hydroxyphenoxyacetate (700 mg, 3.0 mmol) and MeI(0.280 mL, 4.5 mmol) in DMF (5 mL) at 0° C. was added 10M aq. NaOH (0.320 mL, 3.2 mmol). The mixture was stirred at r.t. for 12 h, then diluted with H2 O and extracted with EtOAc to give ethyl 3-chloro-4-methoxyphenoxyacetate (700 mg).

Workup

  1. additiondiluted with H2 O
  2. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-ca0342b162f244ef8f9f87f4464a2eb1
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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