1-Chloro-4-(chloromethyl)benzene → 3-(4-Chloro-benzyloxy)-phthalic acid dimethyl ester

HRID 1915137Notes

Reaction equation

HRID 1915137 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 669067463-(4-Chloro-benzyloxy)-phthalic acid dimethyl esterYield 109.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.3 g, 6.3 mmol) in acetone (20 mL) and potassium carbonate (2.6 g, 19 mmol) was added 4-chlorobenzyl chloride (1.1 g, 6.6 mmol) and refluxed overnight. The solvent was evaporated and the residue was partitioned between water (100 mL) and ethyl acetate (150 mL) and washed with water (2×100 mL). The combined organic phases was dried, concentrated and purified by flash column chromatography (EtOAc/Hexane) to give 3-(4-chloro-benzyloxy)-phthalic acid dimethyl ester (2.3 g, 110% crude yield). The product was used in the next step without further purification.

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water (100 mL) and ethyl acetate (150 mL)
  4. washwashed with water (2×100 mL)
  5. customThe combined organic phases was dried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-49537bdc4df24cef8ed91a8e77707ea3
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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