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

HRID 860651Notes

Reaction equation

HRID 860651 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-061c43d2dd0e427a9fd96a6b2d184653
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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