2-Methyl-1-naphthol → HCID 12723019, compound

HRID 1590556Notes

Reaction equation

HRID 1590556 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:12].ClC[CH:15]([O:18]C(CCl)CCl)CCl>ClCCl>[OH:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH:15]=[O:18])=[CH:11][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 240552-Methyl-1-naphtholHCID 93323Bis(1,3-dichloroisopropyl ether)

Product 1

HCID 12723019HCID 12723019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-1-naphthol (7.0 g, 44.2 mmole) and 1,1-dichloromethyl-methyl ether (7.12 g, 61.9 mmol) were dissolved in dry dichloromethane (150 ml). To the stirred solution stannic chloride (20.72 g, 79.6 mmole) was added dropwise at -58°, the mixture stirred for 45 minutes, and warmed to +10°. It was poured onto ice-water (200 ml) and extracted with ethyl acetate (2×100 ml). The extract was washed with aqueous saturated sodium chloride solution, dried and evaporated. The residue solidified on trituration under diethyl ether:n-pentane (1:10) mixture, was filtered off and chromatographed on silica gel using dichloromethane as eluant to give 4-hydroxy-3-methyl-1-napthaldehyde as a buff coloured crystalline solid, (5.3 g, 64.4%), m.p. 160°-61°.

Workup

  1. temperaturewarmed to +10°
  2. additionIt was poured onto ice-water (200 ml)
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. washThe extract was washed with aqueous saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. filtrationwas filtered off
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-508ab1faa07145e0abe50e8bad0d7c43
Source dataset
uspto-grants-1993_04
Patent number
US05204336

Reaction notes

Loading…