Methyl iodide → HCID 12898558, compound

HRID 1680253Notes

Reaction equation

HRID 1680253 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:9]1[CH:21]=[C:20]([CH3:22])[C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([CH3:23])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].[CH3:28]I>CN(C)C=O>[F:1][C:2]([F:24])([F:25])[C:3]([C:9]1[CH:21]=[C:20]([CH3:22])[C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([CH3:23])[CH:10]=1)([O:8][CH3:28])[C:4]([F:6])([F:5])[F:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12898550HCID 12898550, compound

Product 1

HCID 12898558HCID 12898558, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To ethyl 2-[4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylphenoxy]acetate (6.0 g=16 mmol) in 60 ml dry dimethylformamide add sodium hydride dispersion in mineral oil (0.85 g=18 mmol). Stir 1 hour and add methyl iodide (3.0 g=21 mmol). Let stir 2 hours and partition between water and ether. Wash the ether layer with water, dry and concentrate. Recrystallize from ether-hexane to obtain ethyl 2-[4-(hexafluoro-2-methoxy-2-propyl)-2,6-dimethylphenoxy]acetate, m.p. 97°-98° C.

Workup

  1. stirringLet stir 2 hours
  2. custompartition between water and ether
  3. washWash the ether layer with water
  4. customdry
  5. concentrationconcentrate
  6. customRecrystallize from ether-hexane

Sources & evidence

ORD record
ord-3fad7b8cec59469586313123b80d2209
Source dataset
uspto-grants-1981_06
Patent number
US04272550

Reaction notes

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