Hydrochloric Acid → 3-Cyano-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester

HRID 2072609Notes

Reaction equation

HRID 2072609 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:36])[C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])=[C:26](Br)[CH:25]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:37][N:38](C)C=O.Cl.O>C1(C)C=CC=CC=1>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:36])[C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])=[C:26]([C:37]#[N:38])[CH:25]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 542993093-Bromo-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester

Product 1

HCID 147668273-Cyano-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of this 3-bromo-4-(2'-methylbutyl)benzoic acid 4-octyloxy-4'-biphenylyl ester (5.5 g, 0.01 mol), cuprous cyanide (1.1 g, 0.06 mol) and dimethylformamide (20 ml) was heated to 145°-147° C., following by agitating it for 6 hours, adding a mixture of ferric chloride (4 g), hydrochloric acid (1 ml) and water (7 ml), keeping the mixture at 60°-70° C. for 15 minutes, feeding it into ice water, adding toluene, sufficiently agitating the mixture, transferring it into a separating funnel, several times washing the resulting organic layer with water, drying it over anhydrous MgSO4, distilling off toluene and recrystallizing the residue from ethanol (50 ml) to obtain the objective 3-cyano-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester (1.7 g). The phase transition points of this product were as follows: ##STR46##

Workup

  1. temperaturewas heated to 145°-147° C.
  2. additionadding
  3. customat 60°-70° C.
  4. customfor 15 minutes
  5. stirringsufficiently agitating the mixture
  6. washseveral times washing the resulting organic layer with water
  7. dry with materialdrying it over anhydrous MgSO4
  8. distillationdistilling off toluene
  9. customrecrystallizing the residue from ethanol (50 ml)

Sources & evidence

ORD record
ord-96cb0a630d2a4f9497fedc2c137a7e7d
Source dataset
uspto-grants-1990_04
Patent number
US04913838

Reaction notes

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