2,7-Dimethoxy-1-naphthaldehyde → 2-Hydroxy-7-methoxy-1-naphthaldehyde

HRID 394649Notes

Reaction equation

HRID 394649 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[C:4]=1[CH:15]=[O:16].C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[C:4]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 2932152,7-Dimethoxy-1-naphthaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 105360972-Hydroxy-7-methoxy-1-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After the dimethoxylated product obtained in Step B (2 g: 9.25 mmol) has been dissolved in anhydrous dichloromethane, 97% BBr3Me2S complex (2.98 g: 9.25 mmol 1 eq.) is introduced at ambient temperature. After 35 minutes of stirring, hydrolysis is carried out with a saturated solution of sodium hydrogen carbonate (pH=8). The product is extracted with dichloromethane and then purified on a silica column AcOEt/PE (3/7).

Workup

  1. addition97% BBr3Me2S complex (2.98 g: 9.25 mmol 1 eq.) is introduced at ambient temperature
  2. customhydrolysis
  3. extractionThe product is extracted with dichloromethane
  4. custompurified on a silica column AcOEt/PE (3/7)

Sources & evidence

ORD record
ord-5a25d206ef51471592c996cba73b51c0
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

Loading…