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

HRID 37690

반응식

HRID 37690 반응식
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]

참가 물질

5

반응물 2

HCID 5416072-Dimethylaminomethyl-4-chloro-1-naphtholHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 240552-Methyl-1-naphthol수율 95%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ea50569006154a6db29649a8e68c5e0a
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420362

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