2-Chloroethanol → 4-(2-Hydroxyethoxy)-3-methylmandelic acid

HRID 22502

反応式

HRID 22502 の反応式
[OH-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][C:5]=1[CH3:15].Cl[CH2:17][CH2:18][OH:19].Cl>O>[OH:19][CH2:18][CH2:17][O:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][C:5]=1[CH3:15]

参加物

6

反応物 4

HCID 342-Chloroethanol2 回HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide3 回HCID 233614054-Hydroxy-3-methylmandelic acid

生成物 1

HCID 199304424-(2-Hydroxyethoxy)-3-methylmandelic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

反応条件

温度
70 °C

実験手順

A solution of 8.0 g (200 mmol) of sodium hydroxide in 15 ml of water is added dropwise over a period of one hour to a solution of 18.2 g (100 mmol) of 4-hydroxy-3-methylmandelic acid (Example 13), 4.0 g (100 mmol) of sodium hydroxide and 13.4 ml (200 mmol) of 2-chloroethanol in 60 ml water heated to 70° C. Another 6.7 ml (100 mmol) of 2-chloroethanol and 4.0 g (100 mmol) of sodium hydroxide in 10 ml of water are then added. After another 15 minutes, the reaction mixture is acidified with concentrated hydrochloric acid and extracted twice with ethyl acetate. The organic phases are washed with water, combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. This gives 23.0 g (about 100%) of 4-(2-hydroxyethoxy)-3-methylmandelic acid as a yellowish resin (compound (203), Table 2).

後処理

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phases are washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a vacuum rotary evaporator

出典と根拠

ORDレコード
ord-5a8f3738e8b54083859973ad6d386fe0
出典データセット
uspto-grants-1995_06
特許番号
US05428162

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