5-(Benzyloxy)-2-hydroxybenzaldehyde → 4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol

HRID 1609966Notes

Reaction equation

HRID 1609966 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:14]([OH:15])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8783625-(Benzyloxy)-2-hydroxybenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 222611734-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenolYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenol (Kappe, T.; Witoszynskyj, T. Arch. Pharm., 1975, 308 (5), 339-346) (1.14 g, 5.00 mmol) in THF (15 mL) was cooled in a dry ice/acetone bath and treated dropwise with phenyllithium (7.5 mL, 13.5 mmol, 1.8M in cyclohexane/ethyl ether 70/30). The reaction mixture was allowed to warm gradually to ambient temperature. After 18 h, the reaction was quenched with aqueous saturated NH4Cl solution (1 mL) and partitioned between EtOAc (50 mL) and 1N HCl (20 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated to a brown oil (2.3 g). The crude product was purified by flash chromatography using hexanes:ethyl acetate (3:1 to 2:1) to give a pale yellow oil (1.42 g, 93%): 1H NMR (400 MHz, CDCl3) δ 2.79 (s, 1H), 4.92 (s, 2H), 5.95, (s, 1H), 6.51 (s, 1H), 6.81 (d, 3H, J=1.5 Hz), 7.28-7.38 (s, 10H); MS (ES) m/e 305 [M−1].

Workup

  1. customthe reaction was quenched with aqueous saturated NH4Cl solution (1 mL)
  2. custompartitioned between EtOAc (50 mL) and 1N HCl (20 mL)
  3. washThe organic layer was washed with brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a brown oil (2.3 g)
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-4730ca70f1884f72887c412b2fad3f0c
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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