Water → 3-(4-Chloromethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 854546Notes

Reaction equation

HRID 854546 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][C:7]=1[CH3:14].C(N(CC)CC)C.S(Cl)([Cl:25])=O.O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:25])=[CH:8][C:7]=1[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 574319763-(4-Hydroxymethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

Product 1

HCID 574319813-(4-Chloromethyl-2-methyl-phenyl)-propionic Acid Methyl EsterYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (1.02 g, 4.90 mmol) in anhydrous CH2Cl2 (15 mL) is added triethylamine (0.75 mL, 5.38 mmol) followed by thionyl chloride (0.40 mL, 5.48 mmol). The mixture is allowed to warm to RT overnight. Water is added, and the mixture is extracted with CH2Cl2. The organics are dried with MgSO4 and concentrated. The crude material is purified by flash chromatography to yield the title compound (1.01 g, 91%).

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialThe organics are dried with MgSO4
  3. concentrationconcentrated
  4. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-1dcbed1c3f3648968ebbfb66f5f2f357
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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