1,2-Dichloroethane → 2-Chloro-4-methoxyphenylacetic acid methylester

HRID 1095920Notes

Reaction equation

HRID 1095920 reaction equation
CO.[CH2:3](Cl)CCl.[Cl:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=[O:18].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:3][O:18][C:17](=[O:19])[CH2:16][C:9]1[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=1[Cl:7]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 887MethanolHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acid

Product 1

HCID 573835072-Chloro-4-methoxyphenylacetic acid methylesterYield 88%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methanol (12.13 mL), DMAP (609 mg), EDC (19.11 g), and triethylamine (13.88 mL) were added under cooling (ice) to a solution of (2-chloro-4-methoxy-phenyl)-acetic acid (20.00 g, [CAS Reg. No. 91367-09-8]) in CH2Cl2 (400 mL). The reaction mixture was stirred overnight at r.t. The reaction mixture was poured into ice/water and acidified with 1M aqueous HCl to pH 2. The aqueous layer was extracted two times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a colorless oil (18.77 g, 88%). MS (m/e)=215.1 [MH+].

Workup

  1. extractionThe aqueous layer was extracted two times with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-5d5b51d50f754833bf2df344614e620d
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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