Dichloromethane → HCID 14370895, compound

HRID 2165335Notes

Reaction equation

HRID 2165335 reaction equation
ClCCl.[CH2:4]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(Cl)(=O)C(Cl)=O.[C:32]([O:42][CH3:43])(=[O:41])[CH:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)O>N1C=CC=CC=1>[CH2:4]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH:33]([C:32]([O:42][CH3:43])=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:24])=[CH:18][CH:17]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 78066(+-)-Methyl mandelateHCID 14370883HCID 14370883, compound

Product 1

HCID 14370895HCID 14370895, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a dichloromethane (20 ml) solution of 4-undecyloxyphenylacetic acid (2 g, 7 mmol.) was added dropwise oxalyl chloride (1 ml). The reaction solution was stirred at 50° C. for one hour, which was then cooled, followed by concentration under reduced pressure The concentrate was dissolved in dichloromethane (10 ml), and the solution was added dropwise to a dichloromethane (10 ml) solution of methyl mandelate (1.1 g, 6.5 mmol.). To the reaction solution was added pyridine (2 ml), and the mixture was stirred at room temperature for two hours, to which was then added water (50 ml), followed by extraction with IPE. The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (developing solvent: IPE) to give methoxycarbonylphenylmethyl 4-undecyloxyphenylacetate (2-g, 1.4 g, 43%).

Workup

  1. temperaturewhich was then cooled
  2. concentrationfollowed by concentration under reduced pressure The concentrate
  3. dissolutionwas dissolved in dichloromethane (10 ml)
  4. stirringthe mixture was stirred at room temperature for two hours, to which
  5. extractionadded water (50 ml), followed by extraction with IPE
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by means of a silica gel chromatography (developing solvent: IPE)

Sources & evidence

ORD record
ord-b26a2946afe34a3597f71cd2f0050878
Source dataset
uspto-grants-1990_07
Patent number
US04939274

Reaction notes

Loading…