Carbon Dioxide → p-Menthane-3-carboxylic acid

HRID 252688

反応式

HRID 252688 の反応式
[Mg].C(COCCOCCOC)CCC.II.BrCCBr.[CH:21]1([CH3:31])[CH2:26][CH2:25][CH:24]([CH:27]([CH3:29])[CH3:28])[CH:23](Cl)[CH2:22]1.[C:32](=[O:34])=[O:33]>>[CH:21]1([CH3:31])[CH2:26][CH2:25][CH:24]([CH:27]([CH3:29])[CH3:28])[CH:23]([C:32]([OH:34])=[O:33])[CH2:22]1

参加物

7

反応物 6

HCID 280Carbon DioxideHCID 807IodineHCID 78391,2-DibromoethaneHCID 859512-Chloro-4-methyl-1-(1-methylethyl)cyclohexane2 回HCID 5462224MagnesiumHCID 865944651-Methoxy-2-[2-(pentyloxy)ethoxy]ethane

生成物 1

HCID 97896p-Menthane-3-carboxylic acid

反応条件

温度
90 °C

実験手順

Magnesium (37 g, 50 mesh), butyl diglyme (600 g), and iodine (0.1 g) were added under nitrogen to a 1-liter flask equipped with agitation, addition funnel, off-set adaptor for thermometer, gas addition tube, and condenser. The mixture was stirred for 30 min. at 90° C., and then 1,2,-dibromo ethane (2 cc) was slowly added. p-Menth-3-yl chloride (200 g) was then added at a rate of 50 g/hr (0.32 mole/hr). After approximately ½ of the p-menth-3-yl chloride was added, carbon dioxide was concurrently added by bubbling the carbon dioxide into the mixture at a rate of 15.91 g/hr (0.36 mole/hr), and at a temperature of 90° C. Addition of the carbon dioxide was continued at a temperature of 90° C. until 30 min. after all of the p-menth-3-yl chloride was added. After carbonation was complete, the resultant mixture was hydrolyzed with aqueous hydrochloric acid (1:1 hydrochloric acid/water), and the resultant oil layer was neutralized with trisodium phosphate. VPC analysis showed a yield of 93.18% by weight of p-menthane-3-carboxylic acid.

後処理

  1. customequipped with agitation, addition funnel, off-set adaptor for thermometer, gas addition tube, and condenser
  2. customby bubbling the carbon dioxide into the mixture at a rate of 15.91 g/hr (0.36 mole/hr)
  3. customat a temperature of 90° C
  4. additionAddition of the carbon dioxide
  5. waitwas continued at a temperature of 90° C. until 30 min.
  6. additionafter all of the p-menth-3-yl chloride was added

出典と根拠

ORDレコード
ord-46984eed74024c00b9f54f1613be8efc
出典データセット
uspto-grants-2011_01
特許番号
US07868200B2

関連ノート

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