Hydrochloric Acid → 2,3-Difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenyl

HRID 1289378Notes

Reaction equation

HRID 1289378 reaction equation
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(O)C.Cl.[F:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]Br)=[CH:30][CH:29]=1>O1CCCC1>[F:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([O:13][CH2:14][CH3:15])=[O:12])=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 189208562,3-Difluoro-4'-(11-bromoundecyl)oxybiphenyl

Product 1

HCID 189208382,3-Difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenylYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 0.62 g of sodium ethoxide, 1.5 g of diethyl malonate, and 50 ml of dry ethanol were placed in a 100 ml flask whose content was replaced with argon. Then, 20 ml of tetrahydrofuran solution in which 4 g of 2,3-difluoro-4'-(11-bromoundecyl)oxybiphenyl was dissolved was added dropwise to the reaction mixture, and the resultant reaction mixture was stirred under reflux for 8 hours. The reaction mixture was poured into diluted hydrochloric acid, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene) to obtain 4 g of 2,3-difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenyl (Y: 84.7%). The compound thus obtained had a purity of 99.8% by GC.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. customthe resultant reaction mixture
  3. temperatureunder reflux for 8 hours
  4. extractionan organic layer was extracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-737b20e0ab864dca948446b5066447cd
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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