Benzyl Alcohol → HCID 15606559, compound

HRID 2295392Notes

Reaction equation

HRID 2295392 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:3]=1.[CH3:15]C1C(C2C=CC=CN=2)=NC(C)=CC=1.CC1C(C2C=CC=CN=2)=NC=C(C)C=1.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C)P(=O)(N(C)C)N(C)C>[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[CH:1]([C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:3]=1)=[CH2:15]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 11008603HCID 11008603, compound2×HCID 12232398HCID 12232398, compoundHCID 12232399HCID 12232399, compound2×

Product 2

HCID 244Benzyl AlcoholHCID 15606559HCID 15606559, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

500 g (2.75 mols) of a mixture of isomers, consisting of 4,6-dimethyl-2,2'-bipyridine (45% by weight), 3,6-dimethyl-2,2'-bipyridine (45% by weight) and 3,5-dimethyl-2,2'-bipyridine (10% by weight), are reacted in accordance with the procedure of Example 1(a). The crude product formed is heated under 133 to 400 Pa for 2 hours at 120° to 125° C. and then for 45 minutes at 170° C. (bath temperature). 299 g of a distillate are thus obtained which has a boiling range of 65°-107° C. and which is composed of 65% by weight of 3,6-dimethyl-2,2'-bipyridine, 7% by weight of 3,5-dimethyl-2,2'-bipyridine as well as 17% by weight of benzyl alcohol and 10% by weight of hexamethylphosphoric acid triamide. The residue is heated under 0.1 Pa and, in a boiling range of 48° -170° C., a mixture distils off which is subjected to a fractional redistillation after di-tert.-butyl-p-cresol has been added as a polymerisation inhibitor. Thus, 51 g of (4-(2-benxyloxy)-ethyl)-6-methyl-2,2'-bipyridine, 11 g of 3,6- and 3,5-dimethyl-2,2'-bipyridine, 105 g of benzyl alcohol and 147 g of 4-vinyl-6-methyl-2,2'-bipyridine (61% of theory) are obtained.

Workup

  1. customare reacted in accordance with the procedure of Example 1(a)
  2. customThe crude product formed
  3. temperatureis heated under 133 to 400 Pa for 2 hours at 120° to 125° C.
  4. custom299 g of a distillate are thus obtained which
  5. temperatureThe residue is heated under 0.1 Pa and, in a boiling range of 48° -170° C.
  6. customa mixture distils off which
  7. distillationis subjected to a fractional redistillation after di-tert.-butyl-p-cresol
  8. additionhas been added as a polymerisation inhibitor

Sources & evidence

ORD record
ord-0932daeb78f74618b9c0ce812ac8d3e6
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

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