HCID 20545903, compound → HCID 20545898, compound

HRID 2059310Notes

Reaction equation

HRID 2059310 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([CH3:22])([CH3:21])[CH2:9]2)=[CH:4][CH:3]=1>C(O)(=O)C.Br>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([CH3:22])([CH3:21])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 20545903HCID 20545903, compound

Product 1

HCID 20545898HCID 20545898, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 4-(4-chlorophenyl)-7-methoxy-2,2-dimethyl-1-tetralone (16.1 g) in acetic acid (75 ml) and hydrobromic acid (48%, 75 ml) was heated under reflux for 16 hr. The solution was concentrated in vacuo, water was added and the mixture extracted with ethyl acetate. The extracts were washed well with water and sodium bicarbonate solution, dried (MgSO4) and the solvent removed to give 4-(4-chlorophenyl)-7-hydroxy-2,2-dimethyl-1-tetralone as a white solid which was used without purification (14.7 g, 91%).

Workup

  1. temperatureunder reflux for 16 hr
  2. concentrationThe solution was concentrated in vacuo, water
  3. additionwas added
  4. extractionthe mixture extracted with ethyl acetate
  5. washThe extracts were washed well with water and sodium bicarbonate solution
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed

Sources & evidence

ORD record
ord-5f7f3b87678f42d99ff69581a926b768
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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