Acetic Anhydride → (3-chlorophenyl)methyl Acetate

HRID 247727

Reaction equation

HRID 247727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1C=CC=CC=1>[C:10]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 701173-Chlorobenzyl alcohol

Product 1

HCID 11217649(3-chlorophenyl)methyl AcetateYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a solution of 84.4 g. (0.592 mole) of 3-chlorobenzyl alcohol in 40 cm3. of benzene 61.5 g. (0.6 mole) of acetic acid anhydride are dropped during 15 minutes while boiling. The reaction mixture is refluxed with 100 cm3. of benzene and washed with 100 cm3. of water thoroughly. The organic phase is separated and evaporated. 105.2 g. of 3-chlorobenzyl acetate are obtained which is suitable to ether-formation. nD20 : 1.5226, yield 96%.

Workup

  1. temperatureThe reaction mixture is refluxed with 100 cm3
  2. washof benzene and washed with 100 cm3
  3. customThe organic phase is separated
  4. customevaporated

Sources & evidence

ORD record
ord-0454e46b42c644bf8206535480ccf04b
Source dataset
uspto-grants-1987_11
Patent number
US04709081

Linked notes

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