Hydrogen Bromide → HCID 15572242, compound

HRID 1449064Notes

Reaction equation

HRID 1449064 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13]C)[CH:12]=1)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:13])[CH:12]=1)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 114470756,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 15572242HCID 15572242, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 6,8-dimethoxy-1-tetralone (3.0 g; 14.0 mmoles) was refluxed overnight with 20 ml of 48% aqueous hydrogen bromide and 20 ml of glacial acetic acid. After cooling to room temperature, the reaction mixture was neutralized with a saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined extracts were dried (brine, magnesium sulfate) and concentrated to afford a red solid which upon trituration with ether gave the desired compound as an off-white solid, 1.77 g (71%); m.p. 209°-210° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried (brine, magnesium sulfate)
  3. concentrationconcentrated
  4. customto afford a red solid which upon trituration with ether

Sources & evidence

ORD record
ord-913e8840b9e04a47843a1d93b5ecf5fd
Source dataset
uspto-grants-1980_02
Patent number
US04188495

Reaction notes

Loading…