Sodium Hydroxide → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 484356

반응식

HRID 484356 반응식
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:16])C)[CH:5]=[CH:4][C:3]1=2.Cl[O-].[Na+].[OH-:21].[Na+]>O1CCOCC1>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([OH:16])=[O:21])[CH:5]=[CH:4][C:3]1=2

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 23665760Sodium Hypochlorite

생성물 1

HCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of 3.8 g (16.5 mmol) of 5,5,8,8-tetramethyl-2-acetyl-5,6,7,8-tetrahydronaphthalene from the preceeding Example 3, 70 ml of 5.25% aqueous sodium hypochlorite (49 mmol), 25 ml of aqueous 2N NaOH and 30 ml of dioxane was heated at 60°-70° C. for 2 hours. The mixture was allowed to cool and the oily organic layer removed. Then the aqueous layer was washed with two portions of ether. The aqueous layer was then treated with sodium metabisulfite solution until the solution was negative to the potassium iodide.starch test. The aqueous layer was then cooled and acidified with H2SO4. The resultant white precipitate was collected by filtration and washed with water. This crude product was further purified by recrystallization from an ethanol/water mixture to give the title compound as a white, crystalline solid. PMR (CDCl3): δ 1.31 (6H, s), 1.32 (6H, s), 1.71 (4H, s), 7.40 (1H, d, J~8.8 Hz), 7.85 (1H, dd, J~8.8 Hz, 1.8 Hz), 8.08 (1H, d, J~1.8 Hz).

후처리

  1. temperaturewas heated at 60°-70° C. for 2 hours
  2. temperatureto cool
  3. customthe oily organic layer removed
  4. washThen the aqueous layer was washed with two portions of ether
  5. additionThe aqueous layer was then treated with sodium metabisulfite solution until the solution
  6. temperatureThe aqueous layer was then cooled
  7. filtrationThe resultant white precipitate was collected by filtration
  8. washwashed with water
  9. customThis crude product was further purified by recrystallization from an ethanol/water mixture

출처 및 근거

ORD 기록
ord-5a17599f165a4566a87c442e896cf4bf
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05231113

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