Hydrochloric Acid → 4-(2-Hydroxy-3-phenoxypropoxy)mandelic acid

HRID 22503

反応式

HRID 22503 の反応式
[C:1]1([O:7][CH2:8][CH:9]2[O:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Na+].[OH:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]([OH:23])[C:20]([O-:22])=[O:21])=[CH:17][CH:16]=1.[OH-].[K+].Cl>CO.O>[OH:11][CH:9]([CH2:8][O:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:10][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]([OH:23])[C:20]([OH:22])=[O:21])=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 31217Phenyl glycidyl etherHCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

生成物 1

HCID 199304474-(2-Hydroxy-3-phenoxypropoxy)mandelic acid収率 53%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

7.5 g (50 mmol) of 2,3-epoxypropyl phenyl ether (phenyl glycidyl ether) are added to a suspension of 10.4 g (50 mmol) of 4-hydroxymandelic acid sodium salt monohydrate, and 300 mg (5.0 mmol) of potassium hydroxide in 25 ml of methanol, and the mixture is refluxed for 8 hours. The homogeneous reaction mixture is then diluted with 300 ml of water, acidified with 25 ml of concentrated hydrochloric acid and extracted three times with dichloromethane. The organic phases are washed with water, combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator to give 8.4 g (53%) of 4-(2-hydroxy-3-phenoxypropoxy)mandelic acid as a yellowish resin (compound (204), Table 2).

後処理

  1. temperaturethe mixture is refluxed for 8 hours
  2. extractionextracted three times with dichloromethane
  3. washThe organic phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator

出典と根拠

ORDレコード
ord-0238d4fb94e6474d902609c0913f4dc0
出典データセット
uspto-grants-1995_06
特許番号
US05428162

関連ノート

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