Toluene → HCID 86657606, compound

HRID 1427195Notes

Reaction equation

HRID 1427195 reaction equation
C([Li])CCC.[CH3:6][C:7]([CH3:10])([O-:9])[CH3:8].[K+:11].C1(C)C=CC=CC=1.[CH3:19][N:20]([CH3:26])[CH2:21][CH2:22][N:23]([CH3:25])[CH3:24]>C1CCCCC1.O>[CH3:6][C:7]([CH3:10])([O-:9])[CH3:8].[K+:11].[CH3:19][N:20]([CH3:26])[CH2:21][CH2:22][N:23]([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium2×

Product 1

HCID 86657606HCID 86657606, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent4×

Procedure

The procedure of Example 10 was repeated except that: 1318 g (≈1.7 liters, 15.66 mole) of cyclohexane was charged to the reactor (15 ppm residual H2O), which was further made anhydrous by the addition of 0.16 g (2.5 mmole) n-butyllithium. The anhydrous cyclohexane was heated to 70° C., upon reaching the set point temperature, a mixture comprised of 10.36 g (0.092 mole) potassium t-butoxide, 94 g (1.12 mole) cyclohexane, 206.3 g (2.24 mole, 31 ppm water) toluene and 55.45 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.477 mole) was charged through the charge vessel and delivered subsurface to the gently agitated (300 rpm) cyclohexane solution. The vessel and line were flushed with a 100 ml aliquot of cyclohexane before charging with 36.14 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.093 mole). All total (the initial charge, the amount used to form the potassium t-butoxide/TMEDA solution and the amount used to flush the charge lines) 1554 g (18.46 mole) of cyclohexane was charged to the reactor prior to initiating the styrene feed. Styrene, 1644 g (15.78 mole) was fed through the 1/16th inch OD feed line over 369 minutes such that the feed velocity was ≈3.78 ft/s with a feed rate of 4.46 g/min. The reaction mixture was quenched with 11.13 g (0.185 mole) isopropyl alcohol in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 1331, Mn: 877, Mw: 1597, Mz: 2608, PD: 1.68, σn=795, nα3=2.624.

Workup

  1. additionwas charged through the charge vessel
  2. customThe vessel and line were flushed with a 100 ml aliquot of cyclohexane
  3. additionAll total (the initial charge

Sources & evidence

ORD record
ord-ea21bff5254c41d7b02d59f4dd566462
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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