Toluene → HCID 67103907, compound

HRID 45424Notes

Reaction equation

HRID 45424 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15](C2C=CC=CC=2)(O)[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]1(C)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[CH:16][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 58238536HCID 58238536, compound

Product 1

HCID 67103907HCID 67103907, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18 (from above), toluene (75 mL) and a crystal of p-toluenesulfonic acid monohydrate was refluxed with H2O removal (Dean-Stark trap) for 2 hr. The mixture was cooled to room temperature and stirred overnight. The mixture was washed with saturated NaHCO3 solution (25 mL), dried over Na2SO4, filtered and the solution concentrated under reduced pressure to give a brown oil. The crude product was absorbed onto silica gel using DCM and dry-loaded on a column of silica gel (60 g) packed in hexanes. The column was eluted with hexanes (300 mL), 0.4% MTBE/hexanes (500 mL), 0.8% MTBE/hexanes (500 mL) and 1% MTBE/hexanes (1000 mL). Product fractions were concentrated under reduced pressure to give 0.6 g of an inseparable mixture of 19 and 2-(benzyoxy)-2′-methoxybiphenyl as a colorless oil.

Workup

  1. washThe mixture was washed with saturated NaHCO3 solution (25 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe solution concentrated under reduced pressure
  5. customto give a brown oil
  6. customThe crude product was absorbed onto silica gel
  7. washThe column was eluted with hexanes (300 mL), 0.4% MTBE/hexanes (500 mL), 0.8% MTBE/hexanes (500 mL) and 1% MTBE/hexanes (1000 mL)
  8. concentrationProduct fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ef39311a6c849249ac42a089b9aae70
Source dataset
uspto-grants-2013_09
Patent number
US08541521B2

Reaction notes

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