Methanol → Methyl 4-chlorophenylacetate

HRID 532789Notes

Reaction equation

HRID 532789 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 104196Methyl 4-chlorophenylacetateYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 2-(4-chlorophenyl)acetic acid (20.0 g, 117 mmol) in dry methanol (235 mL) was treated with 5 drops of concentrated H2SO4 (cat.) at room temperature. The mixture was stirred overnight to completion, and then concentrated in vacuo to about 40 milliliters. The concentrate was partitioned between ether and half saturated NaHCO3 solution. The aqueous portion was back-extracted once with ether, and the organics were combined. The organic portion was washed with water, then brine, dried over MgSO4, and concentrated in vacuo. The material was placed under high vacuum for one hour to afford the pure methyl 2-(4-chlorophenyl)acetate as a pale yellow oil (19.8 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 7.30 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 3.70 (s, 3H), 3.60 (2, 2H).

Workup

  1. concentrationconcentrated in vacuo to about 40 milliliters
  2. customThe concentrate was partitioned between ether and half saturated NaHCO3 solution
  3. extractionThe aqueous portion was back-extracted once with ether
  4. washThe organic portion was washed with water
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. waitThe material was placed under high vacuum for one hour

Sources & evidence

ORD record
ord-823a0a98d783488bbe774516d2bb5dde
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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