Water → 6-Bromo-2-hydroxy-1-naphthaldehyde

HRID 1061882Notes

Reaction equation

HRID 1061882 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.ClC[CH:15]([O:18]C(CCl)CCl)CCl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH:15]=[O:18])=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 271446-Bromo-2-naphthalenolHCID 93323Bis(1,3-dichloroisopropyl ether)

Product 1

HCID 7354576-Bromo-2-hydroxy-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

6-Bromo-2-naphthol (25.33 g) was suspended in dichloromethane (300 ml) and titanium tetrachloride (25.0 ml) was slowly added dropwise under cooling in an ice bath. 1,1-Dichloromethylmethyl ether (10.5 ml) was added dropwise to the reaction mixture and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was poured into iced water and dichloromethane was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed successively with IN hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated to give the title compound (28.17 g) as brown crystals.

Workup

  1. temperatureunder cooling in an ice bath
  2. additionwas added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layers were washed successively with IN hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d2a72496eb4942c8a8abe2505a679c64
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

Loading…