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

HRID 1289379Notes

Reaction equation

HRID 1289379 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

HCID 189208462,3-Difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenylYield 71.6%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-272f1f991dfc43899957c3fe45f07873
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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