Methyl iodide → Methyl 2-(2-(benzyloxy)phenyl)acetate

HRID 1533253Notes

Reaction equation

HRID 1533253 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 519916(2-Benzyloxyphenyl)acetic acid

Product 1

HCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetateYield 60.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-benzyloxyphenyl)acetic acid (36 g) in dimethylformamide (360 ml) were added potassium carbonate (61.2 g) and methyl iodide (31.6 g) successively. After being stirred for 17 hours, the mixture was filtered and the filtrate was poured into aqueous 1N hydrochloric acid solution (1.8 l). The separated oil was extracted with diethyl ether and the organic layer was washed with brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)] to afford methyl (2-benzyloxyphenyl)acetate (23 g).

Workup

  1. filtrationthe mixture was filtered
  2. additionthe filtrate was poured into aqueous 1N hydrochloric acid solution (1.8 l)
  3. extractionThe separated oil was extracted with diethyl ether
  4. washthe organic layer was washed with brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)]

Sources & evidence

ORD record
ord-c860402f31414d30860d1963f6844e5a
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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