2-Phenylethanol → HCID 54297380, compound

HRID 2225629Notes

Reaction equation

HRID 2225629 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].S([O-])(=O)(=O)C.[CH2:21](O)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 60542-PhenylethanolHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54297380HCID 54297380, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride dispersion in mineral oil (0. 175 g) and stirred for 15 minutes. The mesylate of phenethyl alcohol (1.28 g) was added and the mixture was stirred and heated under argon at 60° C. overnight. The cooled mixture was treated with glacial acetic acid (3 drops) and the volatiles were removed under vacuum. The residue was mixed with water, the product was extracted with diethyl ether (3×50 mL) and the organic layers were washed in turn with water. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give crude product. The material was purified by HPLC (dichloromethane-hexane; 3: 1) to provide 0.4 g of 4-[(2-phenylethyl)oxy]-alpha-oxobenzeneacetic acid methyl ester as a colorless oil.

Workup

  1. stirringthe mixture was stirred
  2. customthe volatiles were removed under vacuum
  3. additionThe residue was mixed with water
  4. extractionthe product was extracted with diethyl ether (3×50 mL)
  5. washthe organic layers were washed in turn with water
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give crude product
  10. customThe material was purified by HPLC (dichloromethane-hexane; 3: 1)

Sources & evidence

ORD record
ord-c74bc10684a74ef0a4ef306cf5e9aa5f
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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