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

HRID 31216ノート

反応式

HRID 31216 の反応式
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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2a0c57a492a5401c976d537e4e38579f
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

反応ノート

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