4-Methylbenzaldehyde → 2-(2-Hydroxy-2-p-methylphenylethyl)-3,5,6-trimethylpyrazine

HRID 443330Notes

Reaction equation

HRID 443330 reaction equation
C1([Li])C=CC=CC=1.[CH3:8][C:9]1[N:14]=[C:13]([CH3:15])[C:12]([CH3:16])=[N:11][C:10]=1[CH3:17].[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=1>CCOCC>[OH:25][CH:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:26])=[CH:19][CH:20]=1)[CH2:17][C:10]1[C:9]([CH3:8])=[N:14][C:13]([CH3:15])=[C:12]([CH3:16])[N:11]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 14296TetramethylpyrazineHCID 178506676HCID 178506676, compound

Product 1

HCID 5859372-(2-Hydroxy-2-p-methylphenylethyl)-3,5,6-trimethylpyrazineYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of phenyllithium in 150 milliliters 7:3 benzene-ether (0.1 mole) at 0° C. was slowly added a solution of 13.6 grams of tetramethylpyrazine (0.1 mole). The mixture was stirred at room temperature for 2 hours and heated under reflux for 1.5 hours. The mixture was cooled to 0° C., and a solution of 12.0 grams of p-tolualdehyde (0.1 mole) in 50 milliliters of ether was added dropwise. The reaction mixture was stirred at room temperature for 1 hour and then treated in the manner of Example I. The crude product was crystallized from ether to yield 10.7 grams of product (42%) as fine white needles, m.p. 99°-101° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThe mixture was cooled to 0° C.
  4. stirringThe reaction mixture was stirred at room temperature for 1 hour
  5. additiontreated in the manner of Example I
  6. customThe crude product was crystallized from ether

Sources & evidence

ORD record
ord-320ce71e049946c08c23a48154977ae4
Source dataset
uspto-grants-1981_04
Patent number
US04259969

Reaction notes

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