Water → HCID 20520799, compound

HRID 2058586Notes

Reaction equation

HRID 2058586 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].[CH3:15][C:16](C)([O-])[CH3:17].[K+].C(Br)C=C.O>C(O)(C)(C)C.C1C=CC=CC=1>[CH2:17]([CH:7]1[CH2:6][C:5]2[C:9](=[C:10]([Cl:11])[C:2]([Cl:1])=[C:3]([O:13][CH3:14])[CH:4]=2)[C:8]1=[O:12])[CH:16]=[CH2:15]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 12806958HCID 12806958, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20520799HCID 20520799, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6386tert-ButanolSolvent2×

Conditions

Temperature
20 °C

Procedure

6,7-Dichloro-5-methoxy-2,3-dihydro-1H-inden-1-one (63.5 gm., 0.274 mole) is dissolved in a mixture of dry tert.-butyl alcohol (500 ml.) and dry benzene (1.5 liters). The solution is refluxed and potassium tert.-butoxide (46 gm., 0.301 mole) in dry tert.-butyl alcohol (1 liter) is added as rapidly as possible. The solution is refluxed for another 1/2 hour, cooled to 20° C., stirred and treated with allyl bromide (36 gm., 0.301 mole). The mixture is stirred and refluxed for 4 hours, cooled and treated with water (250 ml.). The crude 2-allyl-6,7-dichloro-5-methoxy-2,3-dihydro-1H-inden-1-one is separated by filtration, washed with water, dried and recrystallized from a mixture of benzene and hexane.

Workup

  1. temperatureThe solution is refluxed
  2. temperatureThe solution is refluxed for another 1/2 hour
  3. stirringThe mixture is stirred
  4. temperaturerefluxed for 4 hours
  5. temperaturecooled
  6. customThe crude 2-allyl-6,7-dichloro-5-methoxy-2,3-dihydro-1H-inden-1-one is separated by filtration
  7. washwashed with water
  8. customdried
  9. customrecrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-63cbcf0b949f406893721069d54d0b25
Source dataset
uspto-grants-1982_03
Patent number
US04317922

Reaction notes

Loading…