Sulfuric Acid → 4-octyloxy-4'-((S)-3-methyl-pentanoyl)biphenyl

HRID 65394

反応式

HRID 65394 の反応式
[CH3:1][CH:2]([CH2:5][CH3:6])[CH2:3]Br.[CH2:7]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#N)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(=O)(=O)(O)[OH:31].C1(C)C=CC=CC=1>CCOCC.O>[CH2:7]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:1][C@@H:2]([CH3:3])[CH2:5][CH3:6])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

7

反応物 4

HCID 1118Sulfuric Acid2 回HCID 1140TolueneHCID 252541-Bromo-2-methylbutaneHCID 104173[1,1'-Biphenyl]-4-carbonitrile, 4'-(octyloxy)-

生成物 1

HCID 136850704-octyloxy-4'-((S)-3-methyl-pentanoyl)biphenyl

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒3 回

実験手順

Sliced Mg (12.4 g, 0.510 mol) and dry ether (50 ml) were placed in a three-neck flask in a dry nitrogen atmosphere and agitated, and to the mixture was dropwise added a solution obtained by dissolving (+)-2-methylbutyl bromide (prepared from (-)-2-methyl-1-butanol and phosphorus bromide) in dry ether (1 l), so as to keep the temperature of the system at 25° C. or lower. After completion of the dropwise addition, the mixture was allowed to stand at room temperature for 30 minutes, followed by dropwise adding a solution obtained by dissolving a commercially available product, 4-octyloxy-4'-cyanobiphenyl (IV) (129 g, 0.42 mol) in dry ether (1 l) so as to keep the temperature of the system at 10° C. or lower, thereafter refluxing for 4 hours, cooling pouring the reaction liquid in water (600 ml), further adding diluted sulfuric acid (conc. sulfuric acid 40 ml +water 80 ml, adding toluene (500 ml), transferring the mixture into a separating funnel, water-washing till the washing liquid became neutral, distilling off the solvent, distilling the residue under reduced pressure, collecting a fraction of bp 245°~255° C./4 mmHg and recrystalling from acetone (30 ml) to obtain 4-octyloxy-4'-((S)-3-methyl-pentanoyl)biphenyl (IIIa1) (24.6 g), which was a smectic liquid crystal exhibiting SC* phase and SA phase, and its phase transition points were as follows as shown in Table 2, column of Example 23:

後処理

  1. additionto the mixture was dropwise added a solution
  2. customobtained
  3. customat 25° C.
  4. additionAfter completion of the dropwise addition
  5. additionby dropwise adding a solution
  6. customobtained
  7. customat 10° C.
  8. temperaturelower, thereafter refluxing for 4 hours
  9. temperaturecooling
  10. additionpouring
  11. washwater-washing till the washing liquid
  12. distillationdistilling off the solvent
  13. distillationdistilling the residue under reduced pressure
  14. customcollecting a fraction of bp 245°~255° C./4 mmHg and recrystalling from acetone (30 ml)

出典と根拠

ORDレコード
ord-e153a6315c0a4414914c455b97d150b8
出典データセット
uspto-grants-1986_09
特許番号
US04614609

関連ノート

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