Ethylene Glycol → 1-(2-Naphthyl)cyclopropanecarboxylic acid

HRID 504367

反応式

HRID 504367 の反応式
[OH-:1].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1CC#N.Br[CH2:17][CH2:18]Cl.[CH2:20]([OH:23])[CH2:21]O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:8]=[CH:9][C:10]=1[C:21]1([C:20]([OH:23])=[O:1])[CH2:18][CH2:17]1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 820082-Naphthylacetonitrile

生成物 1

HCID 235685201-(2-Naphthyl)cyclopropanecarboxylic acid

試薬・触媒・溶媒 1

HCID 66133Benzyl triethylammonium chloride触媒

反応条件

温度
100 °C

実験手順

Sodium hydroxide (50% aqueous solution, 3.20 g, 0.0552 mol) was added to a mixture of 2-naphthylacetonitrile (0.913 g, 0.00546 mol), benzyltriethylammonium chloride (0.09 g, 0.0004 mol), and 1-bromo-2-chloro-ethane (1.58 g, 0.0110 mol) at 50 celsius for 5 h. Then 1,2-ethanediol (10.0 mL, 0.179 mol) was added and the mixture was heated at 100° C. overnight. The mixture was poured into ice-water (30 mL) and was extracted with ethyl ether (2×10 mL). The aqueous phase was acidified (pH=2) with 1N HCl and was extracted with ethyl acetate (4×15 mL). The combined organic phase was washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was the desired product, which was directly used in next step reaction without further purification.

後処理

  1. extractionwas extracted with ethyl ether (2×10 mL)
  2. extractionwas extracted with ethyl acetate (4×15 mL)
  3. washThe combined organic phase was washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customwas directly used in next step reaction without further purification

出典と根拠

ORDレコード
ord-b0770cc97ca6438b91ff5aa7f4ba3328
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

関連ノート

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