Methanol → Methyl 4-chlorophenylacetate

HRID 1675886Notes

Reaction equation

HRID 1675886 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 was concentrated in vacuo to about 40 mL. The concentrate was partitioned between an 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. concentrationwas concentrated in vacuo to about 40 mL
  2. customThe concentrate was partitioned between an 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-690d08bc950f43ab8ba11b2e34af8dfb
Source dataset
uspto-grants-2011_08
Patent number
US08003651B2

Reaction notes

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