Methylenechloride Hexane → 1,2,3,4-Tetrahydro-1,1'-biphenyl

HRID 2227875Notes

Reaction equation

HRID 2227875 reaction equation
C(Cl)Cl.[CH3:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].N([C@@:13]1(O)[C@@H:19](O)[C@H:18](O)[C@@H:17]([CH2:22]O)O[CH:14]1O)=[N+]=[N-]>C(Cl)(Cl)(Cl)Cl>[C:6]1([CH:13]2[CH2:19][CH2:18][CH2:17][CH:22]=[CH:14]2)[CH:5]=[CH:4][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 21226440Methylenechloride HexaneHCID 56617390HCID 56617390, compound

Product 1

HCID 858201,2,3,4-Tetrahydro-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

TLC Rf=0.67 (10% CH2Cl2/hexane); IR (CCl4) 3088 (m),3063 (m),3025 (s), 2938 (s), 2863 (s), 2838 (s), 1656 (w), 1606 (m), 1543 (m); 1H NMR (CDCl3) δ0.85-2.09 (m, 6H), 3.38 (bs, 1H), 5.70 (dd, J=10.0, 2.1, 1H), 5.86-5.88 (m, 1H), 7.16-7.30 (m, 5H); 13C NMR (CDCl3) δ21.2, 22.7, 32.6, 41.8, 125.9, 127.7, 128.2, 128.3, 130.2, 146.6; LRMS (EI) 159 ((M+1), 15), 158 ((M+), 100), 143 (43), 129 (79); HRMS (EI) calculated for C12H14 158.1096 (M+), found 158.1098. The IR, 1H NMR and 13C NMR, and MS matched spectral data reported by Arnold, D. R. and Mines, S. A., Can. J. Chem. 67:689-698 (1989).

Sources & evidence

ORD record
ord-9af6d3d4ed35407cb7fd675cf2cfa369
Source dataset
uspto-grants-2002_07
Patent number
US06414173B1

Reaction notes

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