Synthesis of tert-butyl chloride

Preparation of tert-butyl chloride (2-chloro-2-methylpropane; chlorotrimethylmethane; trimethylchloromethane)

Preparation of tert-butyl chloride (2-chloro-2-methylpropane; propane, 2-chloro-2-methyl-; chlorotrimethylmethane; trimethylchloromethane)

Preparation of tert-butyl chloride (2-chloro-2-methylpropane; propane, 2-chloro-2-methyl-; chlorotrimethylmethane; trimethylchloromethane)

In a 250 ml separatory funnel, 25 grams of anhydrous tert-butyl alcohol (b.p. 82-83° C, m.p. 25° C) and 85 ml of concentrated hydrochloric acid are placed. The mixture is shaken for 20 minutes. The two layers separate and the lower acid layer is discarded. The obtained tert-butyl chloride is washed with 5% sodium bicarbonate solution, then with water and dried with anhydrous calcium chloride or anhydrous calcium sulfate. The crude tert-butyl chloride is filtered and distilled. The fraction boiling at 49-51° C is collected yielding 28 grams of pure tert-butyl chloride.

A text book of practical organic chemistry, by A. I. Vogel, 276, 1974

IUPAC Name

2-chloro-2-methylpropane

InChI

InChI=1S/C4H9Cl/c1-4(2,3)5/h1-3H3

InChI Key

NBRKLOOSMBRFMH-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)Cl

Depositor-Supplied Synonyms

2-Chloro-2-methylpropane, tert-Butyl chloride, 507-20-0, Propane, 2-chloro-2-methyl-, Chlorotrimethylmethane, Trimethylchloromethane, 2-Chloroisobutane, tert-Butylchloride, t-Butylchloride, T-BUTYL CHLORIDE, 2-Methyl-2-chloropropane, 2-Methyl-2-propyl chloride, Tertiary-butyl chloride, 2-Chloro-2-methyl-propane, NSC 6527, 2-Chloro-2-methyl propane, NBRKLOOSMBRFMH-UHFFFAOYSA-N, EINECS 208-066-4, BRN 1730872, AI3-30754, tertbutyl chloride, tert.butyl chloride, tert-C4H9Cl, tert.-butyl chloride, t-butyl hydrochloride, sJPHADIMUP@, Tert- Butyl Chloride, ACMC-1AU2B, DSSTox_CID_3937, UNII-JN2YO95TZ0, AC1L1VB1, DSSTox_RID_77236, JN2YO95TZ0, DSSTox_GSID_23937, C56352_ALDRICH, Propane, 2-chloro-2-methyl, 1-chloro-1,1-dimethylethane, 2-chloranyl-2-methyl-propane, KSC270C1H, CCRIS 9388, CHEMBL346997, 08680_FLUKA, 19780_FLUKA, CTK1H0113, NSC6527, MolPort-000-872-067, WLN: GX1&1&1, LTBB001176, EBD28756, NSC-6527, STR03102, Tox21_200192, ANW-31110, ZINC01693576, AKOS000121885, MCULE-3289240398, RP18564, RTR-018131, TRA-0205716, NCGC00248555-01, NCGC00257746-01, AN-21463, CAS-507-20-0, CJ-28348, KB-22057, DB-050414, LS-119672, TL8003364, TR-018131, FT-0611695, InChI=1/C4H9Cl/c1-4(2,3)5/h1-3H, 4-01-00-00288 (Beilstein Handbook Reference), A828266, 3B4-0467, I14-0981, I14-6746, T7101765, PROPANE,2-CHLORO,2-METHYL TERT.BUTYL,CHLORIDE, 2-Chloro-2-methyl propane; tert-Butyl chloride; Trimethylchloromethane

Removed Synonyms

1,1-Dimethylethyl chloride, CID10486, c0208

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