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Acetic Acid → Levoglucosenone

HRID 335545
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인쇄 미리보기

반응식

HRID 335545 반응식
[CH2:1]1[O:8][C@@H:7]2[O:9][C@H:2]1[CH:3]=[CH:4][C:5]2=[O:6].C(O)(=[O:12])C>Cl>[CH2:1]1[O:8][C@@H:7]2[O:9][C@H:2]1[CH:3]=[CH:4][C:5]2=[O:6].[C@@H:7]12[O:8][CH2:1][C@@H:2]([O:9]1)[C@@H:3]([OH:12])[CH2:4][C:5]2=[O:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 699486Levoglucosenone

생성물 2

HCID 699486LevoglucosenoneHCID 110408151,6-anhydro-3-deoxy-beta-D-erythro-hexopyranos-2-ulose

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

Levoglucosenone, an isomer of HMF, can be produced from woody (lignocellulosic) material through pyrolysis. F. Shafizadeh et al. (Carbohydrate Research, 71, (1979), 169-191) found that heating levoglucosenone in 0.5 M HCl (pH=0.3) in a boiling water bath to reaction completion (2.5 hours) produced HMF in a 16% yield. Heating levoglucosenone in 2 M acetic acid (pH=2.2) produced 1,6-anhydro-3-deoxy-β-D-erythro-hexopyranos-2-ulose, (represented by Formula (I-a)) in a 77% yield, but no HMF.

후처리

  1. customto reaction completion (2.5 hours)
  2. customproduced HMF in a 16% yield

출처 및 근거

ORD 기록
ord-59a1dad330264d2c864a131dc4d734c7
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08884036B2

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