p-Toluenesulfonic acid → 2-Methoxymethoxy-biphenyl

HRID 2215973Notes

Reaction equation

HRID 2215973 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:25][O:26][C:27](OC)(C)C>C(Cl)Cl>[CH3:25][O:26][CH2:27][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 7017(1,1'-Biphenyl)-2-ol

Product 1

HCID 106804202-Methoxymethoxy-biphenylYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure as in Example 1: step a was followed using 2-hydroxybiphenyl (1.70 g, 10 mmol), p-toluenesulfonic acid (190 mg, 1.1 mmol), DCM (5 mL), and dimethoxypropane (5 mL). Analogous aqueous workup yielded the title compound (225 mg, 11%) which was used without further purification. 1H-NMR (CDCl3): δ 7.58 (m, 2H), 7.44 (m, 2H), 7.36 (m, 2H), 7.32 (m, 1H), 7.25 (dd, 1H, J=1.2, 8.1 Hz), 7.12 (dt, 1H, J=1.2, 7.4 Hz), 5.14 (s, 2H), 3.42 (s, 3H).

Sources & evidence

ORD record
ord-2ef28c3c424641b398c122f3a9f160af
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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