Hydroquinone → HCID 86740169, compound

HRID 370427Notes

Reaction equation

HRID 370427 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>[OH-].[Na+].O.O1CCCC1>[C:9]([OH:23])(=[O:2])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2]

Participants

6

Reactant 2

HCID 785HydroquinoneHCID 66986Myristoyl chloride

Product 1

HCID 86740169HCID 86740169, compoundYield 23.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydroquinone (55 g) was dissolved in a solution of sodium hydroxide (20 g) in water (300 ml) and to the resulting solution was added dropwise a solution of tetradecanoyl chloride (123 g) in tetrahydrofuran (150 ml) with cooling. The precipitate formed was filtered off and the filtrate was extracted with ethyl acetate. The extract was thoroughly washed with water to remove unreacted hydroquinone and the solvent was removed. The residue was recrystallized from n-hexane to give hydroquinone monomyristate (20 g). m.p. 75°-78° C.

Workup

  1. temperaturewith cooling
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe extract was thoroughly washed with water
  6. customto remove unreacted hydroquinone
  7. customthe solvent was removed
  8. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-27cd5da558f54e21a1e12e798c82e512
Source dataset
uspto-grants-1985_07
Patent number
US04526779

Reaction notes

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