Hydrochloric Acid → 2,6-Bis(2-chloropropan-2-yl)naphthalene

HRID 434615Notes

Reaction equation

HRID 434615 reaction equation
[ClH:1].[C:2]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([CH3:17])=[CH2:16])[CH:11]=2)[CH:6]=1)([CH3:4])=[CH2:3].N1C=CC=CC=1.[O-]C#N.[Na+].C(Cl)[Cl:29]>[O-]C#N.[Na+].[Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-].O>[Cl:1][C:15]([C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]([C:2]([CH3:4])([Cl:29])[CH3:3])[CH:6]=2)[CH:11]=1)([CH3:17])[CH3:16]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6344Dichloromethane4×HCID 517096Sodium CyanateHCID 147668462,6-Di(prop-1-en-2-yl)naphthalene

Product 1

HCID 204914462,6-Bis(2-chloropropan-2-yl)naphthalene

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178514019HCID 178514019, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

2,6-Bis(-1chloro-1-methylethyl)naphthalene (0.178 mole) was prepared by passing a stream of dry gasous hydrogen chloride through a methylene dichloride suspension of 2, 6-diisopropenylnaphthalene (37.2 g, 0.18 mole) which had previously been cooled to 4° C. After conversion of the diisopropenylnaphthalene to the dichloride the solvent was removed in vacuo at 30° C. leaving an off-white solid. The solid was redissolved in 250 ml. of methylene dichloride, cooled to 4° C. and slowly added to a cooled (4° C.) methylene dichloride suspension of sodium cyanate/zinc chloride catalyst solution. The catalyst solution had previously been prepared by vigorously stirring a suspension of zinc chloride (2.0 g,0.014 mole), pyridine (2.46 g, 0.03 mole), anhydrous, 90% sodium cyanate (34 g 0.47 mole) and 0.25 ml of water in 300 ml methylene dichloride for 2 hours at ambient temperature.

Workup

  1. customAfter conversion of the diisopropenylnaphthalene to the dichloride the solvent was removed in vacuo at 30° C.
  2. customleaving an off-white solid
  3. dissolutionThe solid was redissolved in 250 ml
  4. additionslowly added to
  5. temperaturea cooled
  6. customThe catalyst solution had previously been prepared

Sources & evidence

ORD record
ord-73e7e8fc631d41639bab34681a847774
Source dataset
uspto-grants-1983_08
Patent number
US04399074

Reaction notes

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