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

HRID 969168

반응식

HRID 969168 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 235685201-(2-Naphthyl)cyclopropanecarboxylic acid

시약·촉매·용매 1

HCID 66133Benzyl triethylammonium chloride촉매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b0c9111bbde745dfa1a2ece54dd7fb32
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304081B2

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