Protocatechuic Acid → Propargyl 3,4-Dihydroxybenzoate

HRID 429392

반응식

HRID 429392 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[OH-].[Na+].[CH2:14](Br)[C:15]#[CH:16]>C(O)(C)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH2:16][C:15]#[CH:14])=[O:6]

참가 물질

5

반응물 3

HCID 72Protocatechuic AcidHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

생성물 1

HCID 15545109Propargyl 3,4-Dihydroxybenzoate수율 68%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

Using the above procedure, 3,4-dihydroxybenzoic acid (0.0649 mole) and sodium hydroxide (0.0649 mole) were dissolved in 50% isopropyl alcohol (200 ml). Propargyl bromide (0.0649 mole) was added and the solution was heated to reflux for 6 hours. The solution was then cooled and the isopropyl alcohol was removed under vacuum. The residue was taken up in methylene chloride (200 ml), washed with water (200 ml), saturated sodium bicarbonate, saline and dried over magnesium sulfate. Removal of the solvent yielded crude product, which was recrystallized, from CCI4 to give the pure product. (68.0% yield) m.p. 127-129° C.

후처리

  1. temperaturethe solution was heated
  2. temperatureto reflux for 6 hours
  3. temperatureThe solution was then cooled
  4. customthe isopropyl alcohol was removed under vacuum
  5. washwashed with water (200 ml), saturated sodium bicarbonate, saline
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent
  8. customyielded crude product, which
  9. customwas recrystallized, from CCI4
  10. customto give the pure product

출처 및 근거

ORD 기록
ord-bb23623cd463498b94b6959f677e4cd5
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316500B1

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