2-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanol → 2-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol

HRID 1455021Notes

Reaction equation

HRID 1455021 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:22]([O:25]CC2C=CC=CC=2)=[CH:21][C:10]=1[O:11][CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14])C1C=CC=CC=1>C(O)C.[Pd]>[OH:14][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][O:11][C:10]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 179784692-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanol

Product 1

HCID 179786042-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[2,5-bis(benzyloxy)phenoxy]-1-phenylethanol (3.9 g) in ethanol (175 ml) was hydrogenated in the presence of 10% palladium on charcoal (100 mg) at 30 psi. The catalyst was removed by filtration and the solvent was evaporated under reduced pressure. The residue was recrystallized from the mixture of toluene-ethyl acetate 8:1 (15 ml). The yield of 2-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol is 1.2 g. 1H NMR (DMSO-d6) δ: 3.79 (dd, J 9.6, 8.3 Hz, 1H), 4.00 (dd, J 9.6, 3.6 Hz, 1H), 4.94 (ddd, J 3.6, 8.3, 3.9 Hz, 1H), 5.66 (d, J 3.9 Hz, 1H), 6.18 (dd, J 8.5, 2.3 Hz, 1H), 6.34 (d, J 2.3, 1H), 6.57 (d, J 8.5, 1H), 7.26-7.47 (m, 5H), 7.97 (s, 1H), 8.66 (s, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was recrystallized from the mixture of toluene-ethyl acetate 8:1 (15 ml)

Sources & evidence

ORD record
ord-78f143813fbb4171857fad7b5ed8bf5c
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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