Protocatechuic Acid → Propargyl 3,4-Dihydroxybenzoate

HRID 429392

反応式

HRID 429392 の反応式
[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]

参加物

5

反応物 3

HCID 72Protocatechuic AcidHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

生成物 1

HCID 15545109Propargyl 3,4-Dihydroxybenzoate収率 68%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb23623cd463498b94b6959f677e4cd5
出典データセット
uspto-grants-2001_11
特許番号
US06316500B1

関連ノート

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