2-(2-Hydroxy-2-phenylethoxy)benzene-1,4-diol → 2,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-ol

HRID 31217Notes

Reaction equation

HRID 31217 reaction equation
O[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][O:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[OH:12]>C1(C)C=CC=CC=1>[C:13]1([CH:2]2[O:12][C:6]3[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=3[O:4][CH2:3]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

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

Product 1

HCID 179785732,3-Dihydro-2-phenyl-benzo[1,4]dioxin-6-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(2-hydroxy-2-phenylethoxy)benzene-1,4-diol (1.2 g) in toluene (75 ml) was heated with Amberlyst 15 catalyst (0.5 g) under reflux for 7 hrs. After filtering the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (toluene/ethyl acetate/acetic acid=8:1:1). The yield of 2,3-dihydro-2-phenyl-benzo[1,4]dioxin-6-ol is 0.5 g. 1H NMR (DMSO-d6) δ=4.02 (dd, J=8.5, 11.4 Hz, 1H), 4.35 (dd, J=2.3, 11.4 Hz, 1H), 5.11 (dd, J=8.5, 2.3 Hz, 1H), 6.29 (dd, J=2.8, 8.5 Hz, 1H), 6.32 (d, J=2.8 Hz, 1H), 6.75 (d, J=8.5 Hz, 1H), 7.36-7.47 (m, 5H), 8.99 (s, 1H).

Workup

  1. temperatureunder reflux for 7 hrs
  2. filtrationAfter filtering the solvent
  3. customwas evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (toluene/ethyl acetate/acetic acid=8:1:1)

Sources & evidence

ORD record
ord-351c9713692241819b3ddf2a9c6836ed
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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