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

HRID 988840
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HRID 988840 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

HCID 113599626,8-Di-t-butyl-2-butoxycarbonylchroman수율 87%

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
157.5 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-58ed17b60a5345f48a432d6639dd9ff0
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06635772B2

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