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

HRID 37690

Reaction equation

HRID 37690 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 240552-Methyl-1-naphtholYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-ea50569006154a6db29649a8e68c5e0a
Source dataset
uspto-grants-1995_05
Patent number
US05420362

Linked notes

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