Water → HCID 57431971, compound

HRID 860640Notes

Reaction equation

HRID 860640 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][C:6]=1[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.O>ClCCl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 13979359Methyl (4-methoxy-2-methylphenyl)acetate

Product 1

HCID 57431971HCID 57431971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Methoxy-2-methyl-phenyl)-acetic acid methyl ester (1.5 g, 7.72 mmol) is stirred in dichloromethane (50 mL) at 0 deg. C. Aluminum chloride (4.13 g, 31 mmol) is added followed by ethane thiol (2.9 mL, 38.6 mmol). The resulting mixture is stirred at room temperature for 2 hr. Water (50 mL) is added and the product is extracted into ethyl acetate (3×50 ml), the extracts are combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound as a colorless oil, 1.4 g, 100%. MS M++1 181. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. extractionthe product is extracted into ethyl acetate (3×50 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bc734c1004774fecaa02f252e9b6c0bb
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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