Ethanol → alpha-Methyl-4'-(hydroxy)[1,1'-biphenyl]-4-acetic acid, ethyl ester

HRID 1587583Notes

Reaction equation

HRID 1587583 reaction equation
[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH2:19](O)[CH3:20]>S(=O)(=O)(O)O>[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[C:3]([O:5][CH2:19][CH3:20])=[O:4]

Participants

4

Reactant 2

HCID 702EthanolHCID 18956586alpha-Methyl-4'-(hydroxy)[1,1'-biphenyl]-4-acetic acid

Product 1

HCID 86746942alpha-Methyl-4'-(hydroxy)[1,1'-biphenyl]-4-acetic acid, ethyl esterYield 73.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of α-methyl-4'-(hydroxy)[1,1'-biphenyl]-4-acetic acid (22.0 g, 90.8 mmol) in ethanol (500 mL) and concentrated sulfuric acid (5.0 mL) is refluxed for 30 hours. The solution is concentrated under reduced pressure, is diluted with water (300 mL) and is extracted with ethyl acetate (3×300 mL). The combined ethyl acetate extract is washed with water (400 mL) and brine (400 mL), dried over MgSO4 and is concentrated under reduced pressure to give 20 g of crude product. Purification of this material by column chromatography (25% ethyl acetate in hexane) followed by crystallization from ethyl acetate and hexane gives 18.0 g (73.5%) of crystalline product, m.p. 124°-125° C., MS(CI+ m/z): 271[M+H]+.

Workup

  1. temperatureis refluxed for 30 hours
  2. concentrationThe solution is concentrated under reduced pressure
  3. additionis diluted with water (300 mL)
  4. extractionis extracted with ethyl acetate (3×300 mL)
  5. extractionThe combined ethyl acetate extract
  6. washis washed with water (400 mL) and brine (400 mL)
  7. dry with materialdried over MgSO4
  8. concentrationis concentrated under reduced pressure
  9. customto give 20 g of crude product
  10. customPurification of this material by column chromatography (25% ethyl acetate in hexane)
  11. customfollowed by crystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-0f37ba6fb38f4b978394dc4bba69336c
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

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