Pyridine → (1-Chloro-1-methylethyl)benzene

HRID 434618Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].N(C(C1C=CC2C(=CC=C(C(C)(N=C=O)C)C=2)C=1)(C)C)=C=O.[O-]C#N.[Na+].N1C=CC=CC=1.C(Cl)[Cl:43]>[Cl-].[Zn+2].[Cl-].O>[CH3:3][C:2]([Cl:43])([CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 4 °C

Procedure

α,α-Dimethylbenzylchloride was prepared by passing a stream of dry halogen chloride gas through a solution of methylene dichloride (750 ml) and α-methylstyrene (500 g, 4.2 moles) at 4° C. The reaction and work-up were the same as employed for the preparation of 2,6-Bis(1-isocyanato-1-methylethyl)naphthalene described in Example 8. The resulting monochloride was dissolved in 750 ml. methylene dichloride and was added to a cooled (4° C.) catalyst solution previously prepared from anhydrous, 90% sodium cyanate (389 g, 5.39 moles), pyridine (50 ml, 0.633 mole), zinc chloride (39.15 g, 0.28 mole) and 1 ml H2O in 1075 ml. methylene dichloride. At this point the reaction mixture contained 0.04% by weight of water.

Workup

customat 4° C
customThe reaction

Sources & evidence

ORD record: ord-164ddb4e81b9425789c36befb4b43f15
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04399073

Reaction notes

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