Water → 4-Chloromethyl-2-phenylbenzoic acid methyl ester

HRID 2121163Notes

Reaction equation

HRID 2121163 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1.S(Cl)([Cl:21])=O.[Cl-].[Li+].O>CN(C)C=O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][Cl:21])=[CH:4][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 433294Lithium Chloride2×HCID 10824066Methyl 4-hydroxymethyl-2-phenylbenzoate

Product 1

HCID 544945664-Chloromethyl-2-phenylbenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.5 g (43.3 mmol) of methyl 4-hydroxymethyl-2-phenylbenzoate in 50 mL of N,N-dimethylformamide was added 4.5 mL (62 mmol) of thionyl chloride, and 2.0 g (47 mmol) of lithium chloride. The reaction was complete upon dissolution of the lithium chloride. The solution was poured into 350 mL of water, then extracted with diethyl ether (3×100 mL). The combined diethyl ether layers were back extracted with water (2×100 mL), saturated aqueous sodium bicarbonate solution (1×100 mL), and brine (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to 11.1 g (98%) of 4-chloromethyl-2-phenylbenzoic acid methyl ester as a pale yellow oil.

Workup

  1. extractionextracted with diethyl ether (3×100 mL)
  2. extractionThe combined diethyl ether layers were back extracted with water (2×100 mL), saturated aqueous sodium bicarbonate solution (1×100 mL), and brine (1×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to 11.1 g (98%) of 4-chloromethyl-2-phenylbenzoic acid methyl ester as a pale yellow oil

Sources & evidence

ORD record
ord-de105c496aae46ca9f832e18199535b8
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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