Tetrahydrofuran → 4-Hydroxy-4'-(1-hydroxyethyl)biphenyl

HRID 1587586Notes

Reaction equation

HRID 1587586 reaction equation
C(O[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[O:18]1CC[CH2:20][CH2:19]1.[BH4-].[Na+]>CO>[OH:18][CH:19]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 144384094-Methylcarbonyloxy-4'-hydroxybiphenyl

Product 1

HCID 139308004-Hydroxy-4'-(1-hydroxyethyl)biphenylYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 4-acetoxy-4'-hydroxy-1,1'-biphenyl from part A (5.0 g, 23.6 mmol) in methanol (500 mL) and tetrahydrofuran (30 mL) is treated with sodium borohydride (0.9 g, 23.8 mmol) in portions over 30 minutes at room temperature. After 2 hours, the reaction mixture is concentrated under reduced pressure, diluted with water (400 mL), acidified with 2N HCl and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over MgSO4 and concentrated to a solid residue. Crystallization of the solid from ethyl acetate gives 4.7 g (92.9%) of the title compound, m.p. 159°-160° C.; MS (EI m/z): 214 (M)+ and 199 (b.p. M--CH3)+.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additiondiluted with water (400 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a solid residue
  7. customCrystallization of the solid from ethyl acetate

Sources & evidence

ORD record
ord-300177ea7ab14f11b5bd5c26b0c9fdb8
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

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