2,2-Dimethoxypropane → 4-(Methoxymethoxy)-1,1'-biphenyl

HRID 723018Notes

Reaction equation

HRID 723018 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH3:25][O:26][C:27](OC)(C)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>CCOC(C)=O.ClCCl>[CH3:25][O:26][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 64952,2-DimethoxypropaneHCID 69252-Methylbenzenesulfonic acidHCID 71034-HydroxybiphenylHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 141316644-(Methoxymethoxy)-1,1'-biphenylYield 18%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To an oven-dried flask containing a stirbar was added 4-hydroxybiphenyl (1.70 g, 10 mmol), toluenesulfonic acid (190 mg, 1.1 mmol), dichloromethane (DCM, 5 mL), and dimethoxypropane (5 mL). The solution was heated and stirred at 40° C. for 48 h. Solid NaHCO3 (200 mg) was added, followed by EtOAc (100 mL) and NaOH (1N, 20 mL). The layers were separated and the organic layer was further extracted with NaOH (1N, 12×20 mL), brine (30 mL), and was dried over sodium sulfate. Removal of the solvents in vacuo yielded the title compound (385 mg, 18%) which was used without further purification. 1H-NMR (CDCl3): δ 7.56 (m, 4H), 7.44 (m, 2H), 7.34 (m, 1H), 7.14 (m, 2H), 5.24 (s, 2H), 3.54 (s, 3H).

Workup

  1. additionTo an oven-dried flask containing a stirbar
  2. temperatureThe solution was heated
  3. customThe layers were separated
  4. extractionthe organic layer was further extracted with NaOH (1N, 12×20 mL), brine (30 mL)
  5. dry with materialwas dried over sodium sulfate
  6. customRemoval of the solvents in vacuo

Sources & evidence

ORD record
ord-c8ea920b4a9346f5b8245dcc8bc0084b
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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