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Hydrochloric Acid → 5,7,5',7'-Tetra-tert-butyl-[3,3']bibenzofuranylidene-2,2'-dione

HRID 430724
ノート
印刷プレビュー

反応式

HRID 430724 の反応式
[C:1]([C:5]1[CH:6]=[C:7](C(C)(C)C)[C:8]2[O:12][C:11](=[O:13])[CH:10](O)[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.Cl>ClC1C=CC=CC=1Cl.CN(C)C1C=CN=CC=1>[C:1]([C:5]1[CH:15]=[C:9]([C:9]([CH3:15])([CH3:10])[CH3:8])[C:8]2[O:12][C:11](=[O:13])[C:10](=[C:10]3[C:7]4[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:15]=[C:9]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:8]=4[O:12][C:11]3=[O:13])[C:7]=2[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranone

生成物 1

HCID 534471065,7,5',7'-Tetra-tert-butyl-[3,3']bibenzofuranylidene-2,2'-dione収率 109.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 7239
1,2-Dichlorobenzene
溶媒

反応条件

温度
100 °C

実験手順

10 g of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (prepared as described in Example 1 of U.S. Pat. No. 5,614,572) are introduced in 25 ml of 1,2-dichlorobenzene as initial charge and admixed with 0.5 g of 4-dimethylaminopyridine and 3 ml of thionyl chloride. The solution is then gradually heated to 100° C. so that the evolution of HCl and SO2 remains lively, but still controllable. Thereafter the reaction mixture is stirred at 100° C. for a further ½ h. The temperature is subsequently raised to the reflux point. After 75 min, the 1,2-dichlorobenzene is distilled off, at the end with reduced pressure. The isoxindigo is crystallized out by the addition of 30 ml of acetonitrile to the residue, filtered off, washed with acetonitrile and dried to leave 6.8 g (73% of theory) of 5,7,5′,7′-tetra-tert-butyl[3,3′]bibenzofuranylidene-2,2′-dione of the formula (XV).

後処理

  1. temperatureThe temperature is subsequently raised to the reflux point
  2. waitAfter 75 min
  3. distillationthe 1,2-dichlorobenzene is distilled off, at the end with reduced pressure
  4. customThe isoxindigo is crystallized out by the addition of 30 ml of acetonitrile to the residue
  5. filtrationfiltered off
  6. washwashed with acetonitrile
  7. customdried

出典と根拠

ORDレコード
ord-e99c2fb8f1444889a649ba39e403995f
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06323267B1

反応ノート

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