Acetic Anhydride → HCID 86749234、化合物

HRID 376047

反応式

HRID 376047 の反応式
[I:1]([O-])(=O)=O.[K+].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OC(=O)C)(=O)C.[OH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35]>CC(C)=O>[F:38][C:37]([F:40])([F:39])[S:34]([O-:36])(=[O:35])=[O:33].[C:22]([C:19]1[CH:20]=[CH:21][C:16]2[C:13]3[CH:14]=[CH:15][C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:11][C:12]=3[I+:1][C:17]=2[CH:18]=1)([CH3:25])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 62406Trifluoromethanesulfonic acid2 回HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenyl2 回HCID 23665710Potassium Iodate

生成物 1

HCID 86749234HCID 86749234、化合物収率 2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

Into a 250 ml 3-neck round bottom flask equipped with a mechanical stirrer, thermometer, and inlet was charged with agitation, 4.0 grams (18.8 mmol, 1.0 eq) of potassium iodate, 5.0 grams (18.8 mmol, 1.0 eq) of 4,4'-di-t-butylbiphenyl, and 20 mL of acetic anhydride to form a mixture which was cooled to 0° C. To the mixture was added 5.63 grams (3.32 mL, 37.5 mmol, 2.0 eq) of triflic acid dropwise at such a rate that the reaction temperature did not exceed 10° C. The temperature was kept below 10° C. during the addition by the use of a cooling bath. The reaction mixture was never homogeneous and the 4,4'-di-t-butylbiphenyl did not appear very soluble in the reaction mixture. The reaction mixture turned dark almost immediately upon addition of the triflic acid. The mixture was stirred for about 14 hours at room temperature. The reaction was quenched with approximately 60 mL of water and extracted with methylene chloride. The methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution and concentrated in vacuo. The residue was a dark viscous oil. This material was soluble in ether and could be precipitated with hexanes; however, the precipitate was a brown amorphous powder. Titration with acetone gave a tan solid 0.2 gram (2% yield). Melting point=233°-234° C.

後処理

  1. customInto a 250 ml 3-neck round bottom flask equipped with a mechanical stirrer
  2. customto form a mixture which
  3. customdid not exceed 10° C
  4. additionThe temperature was kept below 10° C. during the addition by the use of a cooling bath
  5. customThe reaction was quenched with approximately 60 mL of water
  6. extractionextracted with methylene chloride
  7. washThe methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution
  8. concentrationconcentrated in vacuo
  9. customcould be precipitated with hexanes

出典と根拠

ORDレコード
ord-aa404a0244c8481dba3e69f4e9267faa
出典データセット
uspto-grants-1996_01
特許番号
US05488147

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