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

HRID 31216Notes

Reaction equation

HRID 31216 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-2a0c57a492a5401c976d537e4e38579f
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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