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Benzoic Acid → 6,8-Di-t-butyl-2-butoxycarbonylchroman

HRID 988840
ノート
印刷プレビュー

反応式

HRID 988840 の反応式
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].C(O)(=O)C1C=CC=CC=1.[C:19]([C:23]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=[C:25]([CH2:33]OCCCC)[C:24]=1[OH:39])([CH3:22])([CH3:21])[CH3:20]>C(O)CCC>[C:29]([C:27]1[CH:26]=[C:25]2[C:24](=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:28]=1)[O:39][CH:2]([C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])[CH2:3][CH2:33]2)([CH3:31])([CH3:32])[CH3:30]
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

5

反応物 3

HCID 243Benzoic AcidHCID 8846Butyl AcrylateHCID 99439272,4-di-t-butyl-6-butoxymethyl-1-hydroxybenzene

生成物 1

HCID 113599626,8-Di-t-butyl-2-butoxycarbonylchroman収率 87%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
157.5 °C

実験手順

Butyl acrylate (771.2 g, 6.02 mol) and benzoic acid (12.26 g, 0.10 mol) were added to 2,4-di-t-butyl-6-butoxymethyl-1-hydroxybenzene (665.2 g, net 586.71 g, 2.01 mol) obtained in Example 1, and the mixture was stirred while heating at 150-165° C. for 30 h. 1-Butanol produced by the reaction was removed. After the completion of the reaction, the reaction mixture was quantitatively analyzed by liquid chromatography according to the internal standard method. As a result, 6,8-di-t-butyl-2-butoxycarbonylchroman was obtained in a yield of 87% (1.74 mol). At this time, 6,8-di-t-butyl-3-butoxycarbonylchroman (a position isomer) was produced in about 8%. For use in the next step, excess butyl acrylate was distilled away under reduced pressure, toluene was added to the residue, and benzoic acid was removed with aqueous sodium hydrogen carbonate solution. The 1H-NMR data of the obtained 6,8-di-t-butyl-2-butoxycarbonylchroman are shown below.

後処理

  1. customobtained in Example 1
  2. customwas removed
  3. customAfter the completion of the reaction

出典と根拠

ORDレコード
ord-58ed17b60a5345f48a432d6639dd9ff0
出典データセット
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06635772B2

反応ノート

読み込み中…

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