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

HRID 1289379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1289379
[BH4-].[Li+].O1CCCC1.Cl.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([C:41](OCC)=[O:42])[C:36](OCC)=[O:37])=[CH:19][CH:18]=1>>[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([CH2:36][OH:37])[CH2:41][OH:42])=[CH:19][CH:18]=1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 4148881Lithium borohydrideHCID 189208382,3-Difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenyl

Produkt 1

HCID 189208462,3-Difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenylAusbeute 71,6 %

Versuchsvorschrift

First, 1.7 g of lithium borohydride and 20 ml of tetrahydrofuran were placed in a 100 ml flask. Then, 60 ml of tetrahydrofuran solution in which 4 g of 2,3-difluoro-4'-[12,12-bis(ethoxycarbonyl)dodecyl]oxybiphenyl was dissolved was added dropwise to the reaction mixture, and the resultant reaction mixture was stirred under reflux for 18 hours. The reaction mixture was poured into cold 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: ethyl acetate/toluene=8/2) and recrystallized from acetone to obtain 2.4 g of 2,3-difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenyl (Y: 71.6%). The compound thus obtained had a purity of 99.6% by HPLC.

Aufarbeitung

  1. additionwas added dropwise to the reaction mixture
  2. customthe resultant reaction mixture
  3. temperatureunder reflux for 18 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: ethyl acetate/toluene=8/2)
  9. customrecrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-272f1f991dfc43899957c3fe45f07873
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750213

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