Sulfuric Acid → 3,4-dihydronaphthalen-1-yl Acetate

HRID 341986Notes

Reaction equation

HRID 341986 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.OS(O)(=O)=O.[C:17](OC(C)=C)(=[O:19])[CH3:18]>>[C:17]([O:10][C:9]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH:11]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7916Isopropenyl acetateHCID 107241-Tetralone

Product 1

HCID 117453803,4-dihydronaphthalen-1-yl AcetateYield 112.3%

Procedure

A mixture of α-tetralone (200 mL, 1.5 mol) and conc. H2SO4 (4 mL) in isopropenyl acetate (1.0 L, 9.08 mol) was heated to reflux overnight. It was cooled to r.t. and filtered through a mixture of celite, NaHCO3 and silica (approx. 1:1:0.2) with EtOAc and concentrated to yield 317.1 g of the crude title product; bp: 90° C./0.5 mm Hg.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered through a mixture of celite, NaHCO3 and silica (approx. 1:1:0.2) with EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0eea12aa22eb4457be97168518329731
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

Loading…