Methanol → (R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

HRID 1620423Notes

Reaction equation

HRID 1620423 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C@@H:4]([OH:8])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C@@H:4]([OH:8])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2733641(-)-2-Chloromandelic acid

Product 1

HCID 11790232(R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetateYield 96%

Procedure

(R)-o-chloromandelic acid (5.6 g) was dissolved in 23.1 ml of methanol, and then a catalytic amount of concentrated sulfuric acid (0.12 ml) was added, and heated to reflux for 2 hrs. After cooling, methanol was evaporated under reduced pressure, and the residue was dissolved in dichloromethane, and washed sequentially with 10% aqueous potassium carbonate solution and water. The dichloromethane solution was dried, and evaporated to dryness, to give 5.79 g of (R)-methyl o-chloromandelate as a clear colorless oil. Yield 96%. 1H-NMR (300 MHz, CDCl3) δ 3.52 (d, 1H, J=4.8 Hz), 3.78 (s, 3H), 5.57 (d, 1H, J=4.5 Hz), 7.26-7.31 (m, 2H), 7.37-7.41 (m, 2H); ESI-MS m/z 222.9 [M+Na]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hrs
  3. temperatureAfter cooling
  4. custommethanol was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed sequentially with 10% aqueous potassium carbonate solution and water
  7. dry with materialThe dichloromethane solution was dried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-fa80d8da577a4ff58de03b7ef4786b9c
Source dataset
uspto-grants-2014_07
Patent number
US08772489B2

Reaction notes

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