Diethyl Ether → 4-Hydroxy-2,3,6-trimethylphenyl acetate

HRID 1953196Notes

Reaction equation

HRID 1953196 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].C(N(CC)CC)C.[CH3:19][CH2:20][O:21]CC.C(Cl)(=O)C>O>[C:20]([O:11][C:3]1[C:2]([CH3:1])=[CH:8][C:6]([OH:7])=[C:5]([CH3:9])[C:4]=1[CH3:10])(=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12785Trimethylhydroquinone

Product 1

HCID 1190244-Hydroxy-2,3,6-trimethylphenyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a mixture of trimethylhydroquinone (15.2 g, 0.1 mol), triethylamine (25.3 g, 0.25 mol) and ether (500 mL) in an ice bath. Slowly add acetylchloride (19.6 g, 0.25 mol) with stirring, allow the reaction to warm to room temperature for an hour, then dilute with water and the separate the layers. Evaporate the ether layer to dryness. Dissolve the resulting diacetate in methanol (300 mL). Add strong ammonium hydroxide (11 mL) and stir the mixture at room temperature overnight. Distill off the solvents under reduced pressure and dissolve the residue in ether. Wash the ether layer with water and evaporate to dryness. Recrystallization from hexane-ether yields 4-acetoxy-2,3,5-trimethylphenol (16.7 g, m.p.=106-107° C.).

Workup

  1. customthe reaction
  2. customthe separate the layers
  3. customEvaporate the ether layer to dryness
  4. dissolutionDissolve the resulting diacetate in methanol (300 mL)
  5. additionAdd strong ammonium hydroxide (11 mL)
  6. stirringstir the mixture at room temperature overnight
  7. distillationDistill off the solvents under reduced pressure
  8. dissolutiondissolve the residue in ether
  9. washWash the ether layer with water
  10. customevaporate to dryness
  11. customRecrystallization from hexane-ether

Sources & evidence

ORD record
ord-4e451afb1bf44ce0b6eb856113310da6
Source dataset
uspto-grants-2000_09
Patent number
US06114572

Reaction notes

Loading…