Acetyl chloride → 4-(Benzyloxy)phenyl acetate

HRID 493037Notes

Reaction equation

HRID 493037 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:16]1CC[CH2:18][CH2:17]1.C(N(CC)CC)C.C(Cl)(=O)C>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:17](=[O:16])[CH3:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 7638MonobenzoneHCID 8028TetrahydrofuranHCID 8471Triethylamine

Product 1

HCID 2387194-(Benzyloxy)phenyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 35.0 g (175.0 mmol) of 4-(benzyloxy)phenol were added 100 ml of dried tetrahydrofuran and 17.7 g (175.2 mmol) of triethylamine, and the mixture was homogeneously dissolved. Next, 13.75 g (175.2 mmol) of acetyl chloride was added to the resultant mixture with cooling with ice. The reaction was conducted at a room temperature for 24 hours. The reaction mixture was poured into 500 ml of an iced water and a solid was formed by stirring. The resultant solid was collected by filtration, dried, and recrystallized from a mixed solvent of hexane/toluene to give 40.3 g (166.5 mmol) of benzyl-(4-acetoxyphenyl)ether.

Workup

  1. dissolutionthe mixture was homogeneously dissolved
  2. temperaturewith cooling with ice
  3. customa solid was formed
  4. filtrationThe resultant solid was collected by filtration
  5. customdried
  6. customrecrystallized from a mixed solvent of hexane/toluene

Sources & evidence

ORD record
ord-acbbba423f3e4164acff0f3177ea85c3
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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