Hydrochloric Acid → Benzene, 1,3-bis(1-chloro-1-methylethyl)-

HRID 2215887Notes

Reaction equation

HRID 2215887 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([CH3:12])=[CH2:11])[CH:5]=1)([CH3:3])=[CH2:2].[ClH:13].[Cl-:14].[Na+].O>>[Cl:13][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([Cl:14])([CH3:3])[CH3:2])[CH:5]=1)([CH3:12])[CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 773531,3-DiisopropenylbenzeneHCID 57417360Sodium chloride; water

Product 1

HCID 11299199Benzene, 1,3-bis(1-chloro-1-methylethyl)-Yield 99%

Procedure

A 40 l V4A steel stirred reactor was initially charged with 18.0 kg (114 mol) of 1,3-diisopropenylbenzene. 10.1 kg (277 mol) of hydrogen chloride were passed in within 8 h at an internal temperature of 5-10° C. (brine cooling) and an internal pressure of 1.1 bar. The remaining HCl was removed by stripping with nitrogen. 26 kg (99%) of 1,3-bis(α-chloroisopropyl)benzene were obtained as a colorless liquid; chlorine content 30.1%; 1H-NMR (CD2Cl2, 360 MHZ): 2.00 (s, 12 H, methyl), 7.29–7.52 (m, 3 H, aromat. H), 7.82-7.83 (m, 1 H, aromat. H).

Workup

  1. customThe remaining HCl was removed

Sources & evidence

ORD record
ord-ab2cee9dee9540499865c9af4f2ed4ca
Source dataset
uspto-grants-2006_09
Patent number
US07109387B2

Reaction notes

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