Acetic Acid → (3-chlorophenyl)methyl Acetate

HRID 247729

Reaction equation

HRID 247729 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:21](O)(=[O:23])[CH3:22]>>[C:21]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 701173-Chlorobenzyl alcohol

Product 1

HCID 11217649(3-chlorophenyl)methyl AcetateYield 93%

Procedure

71 g. of 3-chlorobenzyl alcohol, 60 cm3. of acetic acid and 1 g of p-toluene sulfonic acid are refluxed for 5 hours then the excess of acetic acid distilled off in vacuo. The residue is dissolved in 100 cm3. of 1,2-dichloro ethane and the solution washed with 10% sodium hydrogen carbonate solutin then with water and evaporated. The residue is distilled in vacuo. 85.5 g. of 3-chlorobenzyl acetate are obtained. Boiling point 105°-110° C./933.4 Pa, nD25 : 1.5185, yield 93%.

Workup

  1. distillationthe excess of acetic acid distilled off in vacuo
  2. dissolutionThe residue is dissolved in 100 cm3
  3. washof 1,2-dichloro ethane and the solution washed with 10% sodium hydrogen carbonate solutin
  4. customwith water and evaporated
  5. distillationThe residue is distilled in vacuo

Sources & evidence

ORD record
ord-7c7276304db04af5b4288debb3adce38
Source dataset
uspto-grants-1987_11
Patent number
US04709081

Linked notes

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