Hexanoic Acid → (-)-4-Octyloxy-4'-(1-hexanoyloxyethyl)biphenyl

HRID 1761748

반응식

HRID 1761748 반응식
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([O:24][C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH3:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:30]1(N=C=NC2CCCCC2)CCCC[CH2:31]1.C(O)(=O)CCCCC>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([CH:22]([O:24][C:25](=[O:29])[CH2:26][CH2:27][CH2:28][CH2:30][CH3:31])[CH3:23])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

참가 물질

6

반응물 3

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 19857772(+)-4-Octyloxy-4'-(1-butanoyloxyethyl)biphenyl

생성물 1

HCID 14323892(-)-4-Octyloxy-4'-(1-hexanoyloxyethyl)biphenyl수율 76.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Seven grammes (21 mmol) of (-)-1-(4-octyloxybiphenyl-4'-yl)ethanol prepared in Example 2, 7.5 g (36 mmol) of N,N'-dicyclohexylcarbodiimide and 1.0 g of 4-dimethylaminopyridine were dissolved in 200 ml of dichloromethane. To the solution, 3.4 g (29 mmol) of caproic acid was added and the mixture was stirred for six hours at room temperatre. The deposit crystals were filtered, 200 ml of water was added to the filtrate, and the organic layer was separated. 6N hydrochloric acid was added to the organic solution, and then the solution was neutralized with the aqueous solution of 2N sodium hydroxide. The neutralized solution was washed with water until the washed water became neutral. The solvent and low-boiling fractions were distilled off from the obtained solution. The residue was recrystallized from ethanol and the desired (-)-4-octyloxy-4'-(1-hexanoyloxyethyl)biphenyl 6.8 g was obtained. m.p. 60.8° C., [α]D -78.4° (c 0.88, C2H5OH).

후처리

  1. filtrationThe deposit crystals were filtered
  2. addition200 ml of water was added to the filtrate
  3. customthe organic layer was separated
  4. addition6N hydrochloric acid was added to the organic solution
  5. washThe neutralized solution was washed with water until the washed water
  6. distillationThe solvent and low-boiling fractions were distilled off from the obtained solution
  7. customThe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-6b0d047b83d8438c8acec340794c0b33
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04827052

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