Toluene → HCID 18401299, compound

HRID 862870Notes

Reaction equation

HRID 862870 reaction equation
[CH:1]1([CH2:9][OH:10])[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[CH2:11](Br)[CH:12]=[CH2:13].[OH-].[Na+].[C:17]1(C)[CH:22]=CC=C[CH:18]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:11]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:9][O:10][CH2:22][CH:17]=[CH2:18])[CH2:2][CH2:3]1)[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 1140TolueneHCID 77351,4-CyclohexanedimethanolHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 18401299HCID 18401299, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Into a two liter round-bottom three-neck flask equipped with a mechanical stirrer, reflux condensor, thermocouple, and nitrogen inlet, were placed 1,4-cyclohexanedimethanol (375 g, 2.60 moles), allyl bromide (1100 g, 9.09 moles), toluene (830 mL), sodium hydroxide (300 g, 7.5 mole), and tetra-n-butylammonium bromide (110 g, 0.34 mole). The reaction mixture was stirred at 30°-50° C. for 8 hours and at 70°-80° C. for 10 hours. Gas chromatography analysis showed >99% of the desired product. After cooling, the reaction mixture was poured into 2 liters of water, the layers were separated and the aqueous layer was extracted with 150 mL toluene. The toluene solutions were combined and washed with water until pH ~7. The organic phase was dried over anhydrous sodium sulfate, the solvent was stripped on a rotary evaporator and the product was distilled on a Kugelrohr apparatus at 90°-100° C. under a vacuum 0.03 Torr. A gas chromatorgraphy, mass spectroscopy (K+IDS) and 1H NMR analysis indicated the desired structure with >97% purity. Yield: 385 g (66%), colorless liquid.

Workup

  1. customInto a two liter round-bottom three-neck flask equipped with a mechanical stirrer
  2. temperaturereflux condensor
  3. customthermocouple, and nitrogen inlet, were placed

Sources & evidence

ORD record
ord-394ce955b7d143bf92a90d57be4e1ceb
Source dataset
uspto-grants-1998_02
Patent number
US05719251

Reaction notes

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