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

HRID 1097854Notes

Reaction equation

HRID 1097854 reaction equation
[CH2:1]([OH:3])[CH3:2].C(Cl)CCl.C(N(CC)CC)C.[Cl:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][C:25](O)=[O:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:25](=[O:26])[CH2:24][C:17]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=1[Cl:15])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 702EthanolHCID 8471TriethylamineHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acid

Product 1

HCID 573835082-Chloro-4-methoxyphenylacetic acid ethylesterYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ethanol (8.72 mL, 150 mmol), DMAP (304 mg, 2 mmol), EDC (9.56 g, 50 mmol), and triethylamine (6.91 mL, 50 mmol) were added under cooling (ice) to a solution of (2-chloro-4-methoxy-phenyl)-acetic acid (10.00 g, 50 mmol, [CAS Reg. No. 91367-09-8]) in CH2Cl2 (200 mL). The reaction mixture was stirred at r.t. overnight, then diluted (CH2Cl2), and washed (1N aqueous HCl). The organic layer was dried (Na2SO4), and the solvent was evaporated. Purification of the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-70:30) gave the title compound (7.27 g, 64%).1H NMR (300 MHz, CDCl3) □ 7.18 (1H, d), 6.94 (1H, d), 6.79 (1H, dd), 4.17 (2H, q), 3.79 (3H, s), 3.69 (2H, s), 1.26 (3H, t).

Workup

  1. washwashed (1N aqueous HCl)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was evaporated
  4. customPurification of the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-70:30)

Sources & evidence

ORD record
ord-719fc737f74d4847b0d7ac4baadd9b6a
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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