Sodium Iodide → 4-Allyloxymandelic acid

HRID 22575

反応式

HRID 22575 の反応式
O.[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([O-:11])=[O:10])=[CH:6][CH:5]=1.[OH-].[K+].[I-].[Na+].[CH2:19](Br)[CH:20]=[CH2:21].[CH2:23](Cl)[C:24](=[CH2:26])[CH3:25]>CO>[CH2:21]([O:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)[CH:20]=[CH2:19].[CH2:25]([O:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)[C:24](=[CH2:23])[CH3:26]

参加物

8

反応物 5

HCID 5238Sodium IodideHCID 7841Allyl bromideHCID 112413-Chloro-2-methyl-1-propeneHCID 14797Potassium HydroxideHCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

生成物 2

HCID 199305644-Allyloxymandelic acid収率 70%HCID 199305664-Methallyloxymandelic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

20.8 g (0.10 mol) of 4-hydroxymandelic acid sodium salt monohydrate and 6.6 g (0.10 mol) of potassium hydroxide are dissolved with 1.0 g (6.7 mmol) of sodium iodide in 75 ml of methanol. Then 0.12 mol of allyl bromide (methallyl chloride in the case of methallyl) is added and the reaction mixture is refluxed for 16 hours under nitrogen. The reaction mixture is concentrated on a vacuum rotary evaporator and the residue is acidified with concentrated hydrochloric acid. The product is extracted 3 times with butyl acetate. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from toluene/petroleum ether give 4-allyloxymandelic acids such as 4-allyloxymandelic acid as an amorphous powder (70%) and 4-methallyloxymandelic acid, m.p. 121°-126° (65%).

後処理

  1. temperaturethe reaction mixture is refluxed for 16 hours under nitrogen
  2. concentrationThe reaction mixture is concentrated on a vacuum rotary evaporator
  3. extractionThe product is extracted 3 times with butyl acetate
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator
  7. customCrystallisation of the residue from toluene/petroleum ether

出典と根拠

ORDレコード
ord-c5f188d297c44361a81bdec3606b483a
出典データセット
uspto-grants-1995_06
特許番号
US05428177

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