Heptane → 2-(2-Vinylbenzyloxy-1-methylethyl)-2-oxazoline

HRID 247591Notes

Reaction equation

HRID 247591 reaction equation
C[C@H]1C2C3[C:17]([CH3:20])([CH2:18][CH2:19][CH:11]2C2C(=CC(CC2)=O)C1)[CH:16]([OH:21])CC3.[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[N+:29](C(C)(C)C)(C(C)(C)C)(C(C)(C)C)[C:30]([CH3:33])(C)C.[O-:46]S(O)(=O)=O.[OH-].[Na+]>C1COCC1.O.[Na+].[Cl-]>[CH:19]([CH2:18][C:17]([O:46][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:16]1[O:21][CH2:33][CH2:30][N:29]=1)[CH3:20])=[CH2:11]

Participants

8

Reactant 4

HCID 8900HeptaneHCID 14798Sodium Hydroxide2×HCID 19582CID 19582HCID 9927882t-Bu4NHSO4

Product 1

HCID 686762882-(2-Vinylbenzyloxy-1-methylethyl)-2-oxazoline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a three-neck round bottom flask, 45 g VBC (0.29 mole), 45 g HMEO (0.35 mole), 10 g heptane, and 4 g (t-Bu)4NHSO4 in 100 g THF solvent are added together as organic layers. 70 g NaOH aqueous solution prepared by dissolving 50 wt % of NaOH in H2O saturated with NaCl is added as the aqueous layer. The reaction is carried out at 35°-45° C. for 4 hours. The reaction medium turned deep purple upon agitation. GC analysis of the crude product indicated over 90% conversion. The purification procedure is the same as described above. Due to the high boiling point of SOx, an Aldrich Kugelrohr apparatus is used to distill at a bath temperature of 150° C. under 2-3 mmHg pressure. The distillate is a colorless liquid. The structure is identified by GC and NMR analysis. Thermal polymerization occurs during distillation and results in a crosslinked gel in the distillation flask.

Workup

  1. additionis added as the aqueous layer
  2. customThe purification procedure
  3. distillationto distill at a bath temperature of 150° C. under 2-3 mmHg pressure
  4. distillationThermal polymerization occurs during distillation
  5. customresults in a crosslinked gel in the distillation flask

Sources & evidence

ORD record
ord-019b03db083941d2ab7575a8feaf44c8
Source dataset
uspto-grants-1987_11
Patent number
US04709039

Reaction notes

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