Sulfuric Acid → 4'-Methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylic acid

HRID 1845314Notes

Reaction equation

HRID 1845314 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH:15]3[CH2:19][CH2:18][O:17][CH2:16]3)[CH:11]=[C:10]([C:20]([O:22]C)=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].OS(O)(=O)=O>O1CCOCC1.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH:15]3[CH2:19][CH2:18][O:17][CH2:16]3)[CH:11]=[C:10]([C:20]([OH:22])=[O:21])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 58188199Methyl 4'-methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylate

Product 1

HCID 581882234'-Methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 4′-methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylate (150 mg, 0.46 mmol) in 1,4-dioxane (5 mL) and water (0.5 mL) was added lithium hydroxide (55 mg, 2.3 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then acidified with 2N aq. H2SO4 to pH 4-5 and concentrated in vacuo. The residue was treated with water and extracted with CH2Cl2 (10 mL×3). The combined organic layers were dried (MgSO4), and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.85 (t, J=1.6 Hz, 1H), 7.52 (d, 2H, J=8.4 Hz), 7.48 (dd, 1H=2.4, 1.2 Hz), 7.34 (dd, 1H, J=2.4, 1.6 Hz), 7.28 (d, 2H, J=8.4 Hz), 5.15 (m, 1H), 4.05-3.87 (m, 4H), 2.38 (s, 3H), 2.36-2.27 (m, 1H), 2.20-2.11 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with water
  3. extractionextracted with CH2Cl2 (10 mL×3)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0b09f98ae6d47f2a51c1ee46d9c61fe
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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