Pyridine → HCID 54400462, compound

HRID 918107Notes

Reaction equation

HRID 918107 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([CH3:13])[C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:20](Cl)(=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].CCOCC>C1C=CC=CC=1.O>[C:20]([O:12][C:10]1[CH:9]=[C:8]([CH3:13])[C:6]([OH:7])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:11]=1)(=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 8212Stearoyl chlorideHCID 14258206HCID 14258206, compound

Product 1

HCID 54400462HCID 54400462, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

6.5 G OF 2-T-BUTYL-6-METHYLHYDROQUINONE ARE DISSOLVED IN 65 ML OF BENZENE UNDER NITROGEN AND 2.85 G OF PYRIDINE ARE ADDED. The solution is warmed to 45°C and 10.9 g of stearoyl chloride added. The reaction mixture is maintained at 45°-50°C while stirring for about 3 hours and then cooled to room temperature. 25 ml of benzene, 30 ml of ether and 50 ml of water are added and the mixture shaken in a separatory funnel. The benzene ether layer is then washed twice wth 30 ml portions of water and then dried over magnesium sulfate, filtered and the benzene-ether stripped in vacuo. The residue of 15.6 g was recrystallized twice from methanol and yielding 11.4 g of an off-white crystalline solid having a melting point of 64°-65.5°C.

Workup

  1. temperatureThe reaction mixture is maintained at 45°-50°C
  2. temperaturecooled to room temperature
  3. stirringthe mixture shaken in a separatory funnel
  4. washThe benzene ether layer is then washed twice wth 30 ml portions of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe residue of 15.6 g was recrystallized twice from methanol

Sources & evidence

ORD record
ord-66c416b7582747d0b95f0af1af0fe1d5
Source dataset
uspto-grants-1976_07
Patent number
US03969383

Reaction notes

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