Dicyclohexylcarbodiimide → Pentafluorophenyl 4'-Octyloxy-biphenyl-4-carboxylate

HRID 858337Notes

Reaction equation

HRID 858337 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:25][C:26]1[C:31](O)=[C:30]([F:33])[C:29]([F:34])=[C:28]([F:35])[C:27]=1[F:36].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][C:31]3[C:30]([F:33])=[C:29]([F:34])[C:28]([F:35])=[C:27]([F:36])[C:26]=3[F:25])=[O:23])=[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

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 15548597Pentafluorophenyl 4'-Octyloxy-biphenyl-4-carboxylateYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100 g of 4-octyloxybiphenyl-4′carboxylic acid and 62 g of pentafluorophenol are introduced into 1 liter of dichloromethane. Agitation is carried out for 15 minutes and 69.6 g of N,N′-dicyclohexylcarbodiimide in solution in 500 ml of dichloromethane is added over 15 minutes. The dark beige suspension is agitated for 20 hours at ambient temperature. The dicyclohexylurea is filtered and the filtrate is concentrated. Distillation to constant volume is carried out by the regular addition of ethanol up to the vapour temperature of 74° C. The reaction medium is cooled down to ambient temperature, followed by agitating for one hour, filtering then washing with ethanol. After drying, 145.7 g of sought product is obtained in the form of crystals.

Workup

  1. filtrationThe dicyclohexylurea is filtered
  2. concentrationthe filtrate is concentrated
  3. distillationDistillation to constant volume
  4. additionis carried out by the regular addition of ethanol up to the vapour temperature of 74° C
  5. temperatureThe reaction medium is cooled down to ambient temperature
  6. stirringby agitating for one hour
  7. filtrationfiltering
  8. washthen washing with ethanol
  9. customAfter drying

Sources & evidence

ORD record
ord-9b1f9c04c5f54f36a20ecb00750cedbd
Source dataset
uspto-grants-2006_12
Patent number
US07148322B2

Reaction notes

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