p-Toluenesulfonic acid monohydrate → 3-(2-Quinolin-2-yl-vinyl)-phenol

HRID 892143Notes

Reaction equation

HRID 892143 reaction equation
COCCOC[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[CH:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH:9]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[CH:15]=[CH:14][C:10]1[CH:9]=[C:8]([OH:7])[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 544075821-(2-Methoxyethoxy)-methoxy-3-(2-quinolin-2-yl-vinyl)-benzene

Product 1

HCID 48788413-(2-Quinolin-2-yl-vinyl)-phenol

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(2-methoxyethoxy)-methoxy-3-(2-quinolin-2-yl-vinyl)-benzene (120 mg, 0.35 mmol, example 16) is added p-toluene sulphonic acid monohydrate. (74 mg, 0.39 mmol). The resulting solution is heated to 60° C. and stirred at this temperature for 4 h. The reaction mixture is then cooled, concentrated and the residue taken up in dichloromethane. This solution is washed with sat. NaHCO3 solution, dried over MgSO4 then concentrated to give the title compound as a solid. MS (ESI) 248 (M+H)+.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. concentrationconcentrated
  3. washThis solution is washed with sat. NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-9e6fd853a2dc49e28aaf2c784df32eee
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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