Water → 4-(4-Bromophenyl)-6,7-dimethoxy-2-naphthol

HRID 1771515Notes

Reaction equation

HRID 1771515 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=[O:22])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=[CH:4][CH:3]=1.O>P(=O)(O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([OH:22])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 591887201-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-1,3-dione

Product 1

HCID 591887014-(4-Bromophenyl)-6,7-dimethoxy-2-naphtholYield 90%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

1-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-1,3-dione (3 g, 8 mmol) in 85% phosphoric acid was heated at 70° C. for 20 h. The resulting solution was cooled, poured into water (150 ml) and filtered. The residue was dissolved in dichloromethane (50 ml), washed with water (50 ml), dried (MgSO4) and the solvent was removed under reduced pressure to give the title compound (2.56 g, 90%) as a brown powder.

Workup

  1. temperatureThe resulting solution was cooled
  2. filtrationfiltered
  3. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  4. washwashed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c2da843f6db24b4d942af4ae76a03635
Source dataset
uspto-grants-2016_02
Patent number
US09249136B2

Reaction notes

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