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Hydrochloric Acid → 1-(5,5-Dimethylhexyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 2224862
ノート
印刷プレビュー

反応式

HRID 2224862 の反応式
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:24])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9](C(OCC)=O)[C:8]1=[O:23].Cl>O1CCOCC1>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:24])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][C:8]1=[O:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 68871451Ethyl 4-(5,5-dimethylhexyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalene-2-carboxylate

生成物 1

HCID 692680301-(5,5-Dimethylhexyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one収率 72.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
25 °C

実験手順

A solution of Example 35F (1.84 g, 5.13 mmol) in 1,4-dioxane (20 mL) was treated with aqueous 1N hydrochloric acid solution (20 mL) and refluxed for 3 hours. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated in hot hexane and filtered. The precipitate was dried to give the title compound (1.06 g, 72%). 1H NMR (300 MHz, CDCl3) δ ppm 0.57 (m, 1 H) 0.75 (s, 4.5 H) 0.80 (s, 4.5 H) 1.02 (m, 5 H) 1.51 (s, 1.5 H) 1.56 (s, 1.5 H) 1.84 (m, 1 H) 2.04 (m, 0.5 H) 2.25 (m, 0.5 H) 3.74 (s, 0.5 H) 3.75 (s, 0.5 H) 6.00 (s, 0.5 H) 7.51 (m, 3 H) 8.09 (m, 1 H). (ESI+) m/z 287 (M+H)+.

後処理

  1. temperaturerefluxed for 3 hours
  2. custompartitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in hot hexane
  8. filtrationfiltered
  9. customThe precipitate was dried

出典と根拠

ORDレコード
ord-633337475fd94b299a06e1c031d03f94
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07378414B2

反応ノート

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