Hydrochloric Acid → Methyl 2-[2-(chloromethyl)phenyl]acetate

HRID 1419599Notes

Reaction equation

HRID 1419599 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]C(=O)O1.[CH3:12][O:13]C(Cl)Cl.[CH3:17][OH:18].[ClH:19]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[Cl:19][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[CH2:1][C:17]([O:13][CH3:12])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21004Methane, dichloromethoxy-HCID 780921,4-dihydro-3H-2-benzopyran-3-one

Product 1

HCID 9855748Methyl 2-[2-(chloromethyl)phenyl]acetateYield 68%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1.0 g (6.75 mmol) of 3-isochromanone in 10 ml of toluene was added 2.68 ml (29.7 mmol) of dichloromethyl methyl ether, followed by stirring at room temperature for 24 hours. A mixed solution of 3 ml of methyl alcohol and 1.1 ml of pyridine was added thereto at room temperature. After stirring for an additional 2 hour period, 20 ml of 1N hydrochloric acid was added thereto, and the reaction mixture was extracted with three 20 ml portions of ethyl ether. The ether extracts were combined and washed with two 20 ml portions of 1N hydrochloric acid. Ethyl ether was removed by evaporation, and the residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.912 g (yield: 68.0%) of pure methyl 2-(chloromethyl)phenylacetate.

Workup

  1. customat room temperature
  2. stirringAfter stirring for an additional 2 hour period
  3. extractionthe reaction mixture was extracted with three 20 ml portions of ethyl ether
  4. washwashed with two 20 ml portions of 1N hydrochloric acid
  5. customEthyl ether was removed by evaporation
  6. customthe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-9b19abf544ce4ee7993ce66a65bf7598
Source dataset
uspto-grants-1999_03
Patent number
US05886211

Reaction notes

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