Water → Methyl [2-chloro-4'-(methoxymethoxy)-1,1'-biphenyl-4-yl]acetate

HRID 2076708Notes

Reaction equation

HRID 2076708 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][CH2:12]Cl.[Cl:14][C:15]1[CH:20]=[C:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:18]=[CH:17][C:16]=1[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.O>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[C:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:18]=[CH:17][C:16]=1[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:12][O:11][CH3:10])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 86088067Methyl (2-chloro-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

Product 1

HCID 86761301Methyl [2-chloro-4'-(methoxymethoxy)-1,1'-biphenyl-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (936 μl, 5.37 mmol) and chloromethyl methyl ether (303 μl, 4.02 mmol) were successively added to a solution of methyl (2-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetate (650 mg, 2.68 mmol) obtained in Example (23-3) in methylene chloride (10 ml) under ice-cooling, and the mixture was stirred for 3 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give crude methyl [2-chloro-4′-(methoxymethoxy)-1,1′-biphenyl-4-yl]acetate. According to a method similar to Example (104-1), Example (12-4), Example (40-2), Example (33-5) and Example (17-4), from the compound obtained in the above, the title compound was obtained as a colorless powder (260 mg, six-step total yield: 18%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7573bb4b77694836ab883b391dda87ae
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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