2-Dimethylaminomethyl-4-chloro-1-naphthol → 2-Methyl-1-naphthol

HRID 37690

反応式

HRID 37690 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([CH2:13]N(C)C)[CH:3]=1.[H][H]>C(O)C.[Pd]>[CH3:13][C:4]1[CH:3]=[CH:2][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[OH:12]

参加物

5

反応物 2

HCID 5416072-Dimethylaminomethyl-4-chloro-1-naphtholHCID 178418361HCID 178418361、化合物

生成物 1

HCID 240552-Methyl-1-naphthol収率 95%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of 14.18 g (60 m mole) 4-chloro-2-(dimethylaminomethyl)-1-naphthol (13) and 1.43 g 10% Pd-C in 240 ml ethanol was hydrogenated at 50 psi hydrogen atmosphere for 17 hours at room temperature then filtered over a layer of Celite. The filtrate was concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated, whereby 8.99 g (representing a yield of 95%) 2-methyl-1-naphthol (1) were obtained: 1H NMR (300 MHz, DMSO-d6) δ2.32 (s, 3H), 7.21-7.40 (m, 4H), 7.75 (d, 1H, J=8 Hz), 8.15 (d, 1H, J=8 Hz), 9.01 (s, 1H, exch. with D2O); m/z 158 (M+).

後処理

  1. filtrationthen filtered over a layer of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customwere obtained

出典と根拠

ORDレコード
ord-ea50569006154a6db29649a8e68c5e0a
出典データセット
uspto-grants-1995_05
特許番号
US05420362

関連ノート

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