Methyl Ethyl Ketone → HCID 23333251, compound

HRID 224471Notes

Reaction equation

HRID 224471 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([C:10](=[O:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:5][C:3]=1[OH:4].C(=O)([O-])[O-].[K+].[K+].[CH2:33]([C:35](C)=O)[CH3:34].C(Br)C=C>O>[CH2:35]([O:4][C:3]1[CH:5]=[C:6]([C:10](=[O:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:7]([OH:9])=[CH:8][C:2]=1[CH3:1])[CH:33]=[CH2:34]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 147165312-Methyl-5-hexadecanoylhydroquinone

Product 1

HCID 23333251HCID 23333251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere a mixture of 17.5 g of the keto-compound of step 1, 10.2 g of potassium carbonate and 200 ml of methyl ethyl ketone was refluxed with stirring together with 6.9 g of allyl bromide for 1 hour. After a total refluxing time of 9 h the reaction mixture was mixed with 100 ml of water. The methyl ethyl ketone layer is separated, shaken twice with a 20% by weight sodium chloride solution and dried with sodium sulphate. The residue left after evaporation of the solvent was stirred with methanol, whereupon the precipitate formed was filtered with suction and recrystallized from methanol.

Workup

  1. temperaturewas refluxed
  2. customThe methyl ethyl ketone layer is separated
  3. dry with materialdried with sodium sulphate
  4. waitThe residue left
  5. customafter evaporation of the solvent
  6. stirringwas stirred with methanol, whereupon the precipitate
  7. customformed
  8. filtrationwas filtered with suction
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2d82cbf723b74eba9546114ca420b46a
Source dataset
uspto-grants-1980_11
Patent number
US04232107

Reaction notes

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