Triethylamine → (2-Chloro-4-methylphenyl)methyl acetate

HRID 420755

Reaction equation

HRID 420755 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].CCN(CC)CC.[C:18](OCl)([CH3:20])=[O:19]>ClCCl.O>[C:18]([O:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1])(=[O:19])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12616564Chloro methylformateHCID 15544016(2-Chloro-4-methylphenyl)methanol

Product 1

HCID 58001748(2-Chloro-4-methylphenyl)methyl acetateYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2-chloro-4-methylphenyl)methanol (365 mg, 2.331 mmol) and Et3N (0.390 mL, 2.80 mmol) in Dichloromethane (DCM) (10 mL) at 0° C. AcOCl (0.331 mL, 4.66 mmol) was slowly added and the mixture was left under stirring at 0° C. for 1 hour then at room temperature overnight. Next morning HPLC showed no starting material remaining volatiles were removed under vacuum and resulting crude was dissolved in DCM washed several times with water. Organic layers were dried over Na2SO4 and volatiles removed to afford 453 mg of the final compound as a brown oil.

Workup

  1. customat 0° C
  2. waitthe mixture was left
  3. customat room temperature
  4. customovernight
  5. customwere removed under vacuum
  6. customresulting crude
  7. dry with materialOrganic layers were dried over Na2SO4 and volatiles
  8. customremoved

Sources & evidence

ORD record
ord-257647a2e19c492eab35db16d4826c57
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Linked notes

Loading…