Methanol → Methyl 13-phenyltridecanoate

HRID 1655506Notes

Reaction equation

HRID 1655506 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:27]O>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:27])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1054154413-phenyltridecanoic Acid

Product 1

HCID 19792507Methyl 13-phenyltridecanoate

Procedure

13-Phenyltridecanoic acid (22.4 g, 77 mmol) was reacted for 1 h in methanol (60 ml) and sulfuric acid (2.2 g) under reflux. The reaction mixture was concentrated, poured into H2O (100 ml) and extracted with dichloromethane. The organic layer was washed with H2O, dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue (33 g) was chromatographed on silica gel (Wako Gel C-200) with dichloromethane as eluent to give the title compound as a white solid; yield: 17.6 g; mp 30.5°-31.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into H2O (100 ml)
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue (33 g) was chromatographed on silica gel (Wako Gel C-200) with dichloromethane as eluent

Sources & evidence

ORD record
ord-877c3010943d4783b2b0bec6f782f6eb
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

Loading…