Phenolate Sodium → Ethyl 2-methoxy-5-phenoxybenzoate

HRID 1598983Notes

Reaction equation

HRID 1598983 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[O-:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Na+].IC1C=CC(OC)=C(C=1)C(OC)=O>[Cu-]=O.CC(N(C)C)=O>[CH3:14][O:13][C:5]1[CH:4]=[CH:3][C:2]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 4445035Phenolate SodiumHCID 11011762Methyl 5-iodo-2-methoxybenzoateHCID 18931281Ethyl 5-iodo-2-methoxybenzoate

Product 1

HCID 18931225Ethyl 2-methoxy-5-phenoxybenzoateYield 54.5%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 5-iodo-2-methoxybenzoate (4.1 g, 13.4 mmol), sodium phenoxide (1.7-1.8 g, 15 mmol), copper(I) oxide (1.1 g, 7.5 mmol) and dimethylacetamide (approximately 15 mL) was heated 4 hours with stirring at 180° C. The mixture was filtered, diluted with water and extracted with pentane/diethyl ether (7:3, 2× 100 mL). The combined extracts were washed with dilute sodium hydroxide (3×) and water (1×), dried (K2CO3), filtered and concentrated. The residue was dried (P2O5) under vacuum to give crude product (1.17 g) which was combined with crude product (2.4 g) similarly prepared from methyl 5-iodo-2-methoxybenzoate (6 g, 19.6 mmol). The combined crude product was purified by column chromatography eluting with hexane/acetone (96:4) to give ethyl 2-methoxy-5-phenoxybenzoate (2 g, 7.3 mmol), m.p. 52°-52° C.

Workup

  1. temperaturewas heated 4 hours
  2. filtrationThe mixture was filtered
  3. additiondiluted with water
  4. extractionextracted with pentane/diethyl ether (7:3, 2× 100 mL)
  5. washThe combined extracts were washed with dilute sodium hydroxide (3×) and water (1×)
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dry with materialThe residue was dried (P2O5) under vacuum
  10. customto give crude product (1.17 g) which
  11. customwas purified by column chromatography
  12. washeluting with hexane/acetone (96:4)

Sources & evidence

ORD record
ord-d905fb8bc8944ff09abec0f00e8187d1
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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