Dimethylformamide → 2-Hydroxy-6-octyloxycarbonylnaphthalene

HRID 1033146

Reaction equation

HRID 1033146 reaction equation
F[C:2](F)(F)[CH:3]([OH:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].CN(C)[CH:15]=[O:16].[CH2:18](N(CC)CC)[CH3:19].[C:25]1([C:34]2[CH:39]=[CH:38][C:37]([C:40](Cl)=[O:41])=CC=2)[CH:30]=[CH:29]C(C(Cl)=O)=CC=1>C(Cl)Cl>[OH:10][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[CH:19][CH:9]=[C:8]([C:15]([O:41][CH2:40][CH2:37][CH2:38][CH2:39][CH2:34][CH2:25][CH2:30][CH3:29])=[O:16])[CH:7]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 75374[1,1'-Biphenyl]-4,4'-dicarbonyl dichlorideHCID 978042-Octanol, 1,1,1-trifluoro-

Product 1

HCID 542866972-Hydroxy-6-octyloxycarbonylnaphthaleneYield 105.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Optically active 1,1,1-trifluoro-2-octanol (0.5 g), dimethylformamide (0.35 g) and triethylamine (0.64 g) were dissolved in 20 ml of methylene chloride. To this solution was added in small portions a solution of 4,4'-biphenyldicarboxylic acid dichloride (1.6 g) obtained in 2) of Example 7 in 50 ml of methylene chloride under ice-cooling, and the mixture was stirred for about 20 hours. Next, 2-hydroxy-6-octyloxycarbonylnaphthalene (0.86 g) obtained in 1) was dissolved in 30 ml of methylene chloride and added in small portions to the reaction mixture. The resulting mixture was stirred for about 20 hours.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-637059eaa21948d0bda6664d9a4400bd
Source dataset
uspto-grants-1994_05
Patent number
US05310500

Linked notes

Loading…