Acetone → HCID 70570881, compound

HRID 848435Notes

Reaction equation

HRID 848435 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C:11]2(OCC[O:15]2)[C@@:10]1([CH3:26])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:25])[CH2:23][OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.S(=O)(=O)(O)O>O>[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C@@:10]1([CH3:26])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:25])[CH2:23][OH:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 86738047HCID 86738047, compound

Product 1

HCID 70570881HCID 70570881, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2S*,3R*)-3-benzyloxy-1,1-ethylenedioxy-2-methyl-2-(4'-methyl-5'-hydroxypentyl)-cyclohexane (13.9 g, 0.0384 mol), acetone (150 ml), water (20 ml) and 0.002 N sulfuric acid (50 ml) is refluxed for 18 hours under a nitrogen atmosphere. The reaction mixture is cooled, the acetone evaporated under reduced pressure and the aqueous layer extracted with ether (3×500 ml). The combined organic layers are washed with saturated sodium bicarbonate (100 ml), saturated sodium chloride (2×200 ml) and dried (MgSO4). The solvents are removed to afford (2S*,3R*)-3-benzyloxy-2-methyl-2-(4'-methyl-5'-hydroxypentyl)-cyclohexanone (crude product, 12.2 g, 100%): ir (neat) 3484 (OH), 1709 cm-1 (CO); nmr (CDCl3)δ0.88 (d, J=6 Hz, 3H, -CH-CH3), 1.08 (s, 3H, CH3), 3.42 ##STR36## 4.50 (d of d, J=10 Hz, 2H, Ph-CH2 -O-), 7.2 (s, 5H, aromatic).

Workup

  1. temperatureis refluxed for 18 hours under a nitrogen atmosphere
  2. temperatureThe reaction mixture is cooled
  3. customthe acetone evaporated under reduced pressure
  4. extractionthe aqueous layer extracted with ether (3×500 ml)
  5. washThe combined organic layers are washed with saturated sodium bicarbonate (100 ml), saturated sodium chloride (2×200 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvents are removed

Sources & evidence

ORD record
ord-d503836719f9432cb4521bb79d7657d7
Source dataset
uspto-grants-1981_10
Patent number
US04296035

Reaction notes

Loading…