Menthol → HCID 10494587, compound

HRID 495340Notes

Reaction equation

HRID 495340 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH:13]1([CH3:23])[CH2:18][CH2:17][CH:16]([CH:19]([CH3:21])[CH3:20])[CH:15](O)[CH2:14]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][C@H:15]1[C@H:16]([CH:19]([CH3:21])[CH3:20])[CH2:17][CH2:18][C@@H:13]([CH3:23])[CH2:14]1)=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1254MentholHCID 10868DicyclohexylcarbodiimideHCID 684742-Acetylbenzoic acid

Product 1

HCID 10494587HCID 10494587, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11.36 g (50.0 mmol) 2-acetylbenzoic acid, 4.88 g (40.0 mmol) DMAP and 23.40 g (150.0 mmol) (−)-menthol in 80 ml dichloromethane was cooled in an ice bath before adding a solution of 11.36 g (55.0 mmol) DCC in 40 ml dichloromethane for 15 min. The reaction mixture was maintained with stirring at 40° for 70 h. The precipitate formed during the reaction was filtered and the filtrate washed with HCl (10%, 2×) then with a saturated Na2CO3 solution (2×). The organic phase was dried (Na2SO4), concentrated, chromatographed (SiO2, toluene) and recrystallized in hexane to give 1.96 g (13%) (1R,3R,4S)-3-p-menthanyl 2-acetylbenzoate in the form of white crystals.

Workup

  1. temperatureThe reaction mixture was maintained
  2. customThe precipitate formed during the reaction
  3. filtrationwas filtered
  4. washthe filtrate washed with HCl (10%, 2×)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed (SiO2, toluene)
  8. customrecrystallized in hexane

Sources & evidence

ORD record
ord-bda840e5a4114fefbfd6e041f6f29cc0
Source dataset
uspto-grants-2005_09
Patent number
US06939835B2

Reaction notes

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