Water → 4-Hydroxy-5-methyl-1-naphthalenecarbaldehyde

HRID 654678Notes

Reaction equation

HRID 654678 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([OH:12])=[CH:9][CH:8]=[CH:7]2.[CH3:13][O:14]C(Cl)Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:12][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[C:7]([CH:13]=[O:14])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 122037931-Hydroxy-8-methylnaphthalene

Product 1

HCID 149864524-Hydroxy-5-methyl-1-naphthalenecarbaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24193Titanium TetrachlorideSolvent

Procedure

101.9 g of 8-methyl-1-naphthol was dissolved in 815 ml of dichloromethane, in which 141.6 ml of titanium tetrachloride was gradually dropped under ice-cooling conditions. Thereafter, 93.7 ml of dichloromethyl methyl ether was gradually dropped under ice-cooling conditions. After agitation for 10 minutes, 200 ml of water was gently dropped under ice-cooling conditions. The reaction solution was extracted with ethyl acetate and the resultant organic phase was washed with water. After drying with anhydrous magnesium sulfate, the solvent was distilled off and the resultant crystals were washed with chloroform to obtain 80 g of the captioned compound as brown crystals.

Workup

  1. additionwas gradually dropped under ice-
  2. temperaturecooling conditions
  3. temperaturecooling conditions
  4. temperaturecooling conditions
  5. extractionThe reaction solution was extracted with ethyl acetate
  6. washthe resultant organic phase was washed with water
  7. dry with materialAfter drying with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. washthe resultant crystals were washed with chloroform

Sources & evidence

ORD record
ord-181299dceba14dc783d98e51e33e56ba
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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