Tributyrin → (-)-4-Octyloxy-4'-(1-hexanoyloxyethyl)biphenyl

HRID 1638934

反応式

HRID 1638934 の反応式
O=C(CCC)OCC(OC(=O)CCC)COC(=O)CCC.[CH2:22]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([CH:43]([OH:45])[CH3:44])=[CH:39][CH:38]=2)=[CH:33][CH:32]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(N=C=NC2CCCCC2)CCCCC1.[C:61](O)(=[O:67])[CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:22]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([CH:43]([O:45][C:61](=[O:67])[CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH3:44])=[CH:39][CH:38]=2)=[CH:33][CH:32]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

参加物

7

反応物 4

HCID 6050TributyrinHCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 14297722(-)-4-Octyloxy-4'-(1-hydroxyethyl)biphenyl

生成物 1

HCID 14323892(-)-4-Octyloxy-4'-(1-hexanoyloxyethyl)biphenyl

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Racemic(±)-4-octyloxy-4'-(1-hydroxyethyl)biphenyl (m.p. 110.9°-111.9° C.) and tributyrin were biochemically transesterified. The obtained 7.0 g (21 mmol) of optically active (-)-4-octyloxy-4'-(1-hydroxyethyl)biphenyl (m.p. 123.6° C., [α]D 24.5 -27.0° (c 1.0, CHCl3)), 7.5 g(36 mmol) of N,N'-dicyclohexylcarbodiimide (abbreviated as DCC) and 1.0 g of 4-dimethylaminopyridine (abbreviated as DMAP) 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 temperature. The deposited 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 away from the obtained solution. The residue was recrystallized from ethanol and the desired (-)-4-octyloxy-4'-(1-hexanoyloxyethyl)biphenyl 6.8 g was obtained. The melting point of the obtained biphenyl was 60.8° C. and its specific optical rotation was -78.4° at 25.3° C. for D line (c 0.88, C2H5OH).

後処理

  1. filtrationThe deposited 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 away from the obtained solution
  7. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-366101d6360d4494a89b26d0ef1d3fc0
出典データセット
uspto-grants-1989_11
特許番号
US04882084

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