HCID 54040210, compound → HCID 14419511, compound

HRID 2257440Notes

Reaction equation

HRID 2257440 reaction equation
[CH3:1][C@H:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][C:11]=1[N+]([O-])=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CO.ClCCl>[CH3:1][C@H:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=2)=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 1

HCID 54040210HCID 54040210, compound

Product 1

HCID 14419511HCID 14419511, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The same procedure as that used for saponification of (S)-4-(1-methylheptyloxy)-3-nitro-phenol was used except the reaction was carried out in a methanol/dichloromethane [4:1] mixture at 60° C. Flash chromatography with hexanes/ethyl acetate [93/7] afforded (S)-4'-(1-methylheptyloxy)-4-hydroxybiphenyl (Compound 40, Scheme VIII, R2 =(S)-OCH(CH3)C6H13) as a white solid (mp 100.5° C.); Rf [hexanes/ethyl acetate 90/10]: 0.2; 1H NMR (300 MHz, CDCl3): δ 0.88(t, 3H, J=6.6 Hz), 1.20-1.64(m, 9H), 1.33(d, 3H, J=6.1 Hz), 1.74(m, 1H), 4.38(m, 1H), 5.07(s, 1H), 6.87(d,2H, J=8.5 Hz), 6.93(d, 2H, J=8.5 Hz), 7.42(d, 2H, J=8.5 Hz), 7.44(d, 2H, J=8.5 Hz); 13C NMR (300 MHz, CDCl3): δ 14.02, 19.73, 22.54, 25.51, 29.22, 31.74, 36.45, 74.17, 115.59, 116.16, 127.74, 127.94, 133.22, 133.77, 154.55, 157.31; IR (CHCl3): 3560, 3350(broad), 3020, 2920, 2840, 1610, 1500, 1250, 1220, 1175, 825 cm -1 ; Mass spectrum, m/z(rel.intensity): 298(M+ 11), 186(100), 185(4), 157(4).

Sources & evidence

ORD record
ord-28a19f4954b94af9831a410a56a5d5da
Source dataset
uspto-grants-1997_08
Patent number
US05658493

Reaction notes

Loading…