Sulfuric Acid → Methyl 2-(3-phenoxyphenyl)propanoate

HRID 2055723Notes

Reaction equation

HRID 2055723 reaction equation
O.[O:2]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([O-:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Ca+2].O(C1C=C(C(C)C([O-])=O)C=CC=1)[C:22]1C=CC=CC=1.OS(O)(=O)=O>CO>[CH3:22][O:17][C:16](=[O:18])[CH:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:10]=1)[CH3:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69314396HCID 69314396, compound

Product 1

HCID 529082Methyl 2-(3-phenoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of calcium 2-(3-phenoxy-phenyl)-propionate hydrate (5.00 g, 9.57 mmol) in methanol (150 mL) was added conc. H2SO4 (1.1 mL) and the gelatinous solution heated to reflux for 4 hrs. After cooling, the solution was filtered and evaporated to dryness, the residue dissolved in EtOAc, washed with satd. aq. NaHCO3 soln., dried (MgSO4) and evaporated to yield methyl-2-(3-phenoxy-phenyl)-propionate as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.34 (2H, m), 7.26 (1H, m), 7.11 (1H, m), 6.99-7.02 (4H, m), 6.87 (1H, m), 3.70 (1H, q, J=7.2 Hz), 3.67 (3H, s), 1.58 (3H, d, J=7.2 Hz)

Workup

  1. temperaturethe gelatinous solution heated
  2. temperatureto reflux for 4 hrs
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered
  5. customevaporated to dryness
  6. dissolutionthe residue dissolved in EtOAc
  7. washwashed with satd
  8. dry with material, dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-1bf85085d8394ca38b1eb7882463d411
Source dataset
uspto-grants-2008_02
Patent number
US07332516B2

Reaction notes

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