Acetone → HCID 76484840, compound

HRID 1732841Notes

Reaction equation

HRID 1732841 reaction equation
[CH2:1]([O:8][CH: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][CH: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 86737371HCID 86737371, compound

Product 1

HCID 76484840HCID 76484840, 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)δ 0.88 (d, J=6 Hz, 3H, --CH--CH3), 1.08 (s, 3H, CH3), 3.42 (m, 4H, HO--CH2 --CH--, OH and --CH--O--CH2Ph), 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-8a4713bf0c0f45bda1014c42fe90215c
Source dataset
uspto-grants-1980_12
Patent number
US04239689

Reaction notes

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