Acetone → HCID 53973838, compound

HRID 1605813Notes

Reaction equation

HRID 1605813 reaction equation
C(OCC[C:7]1([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:11][CH2:10][CH2:9][C:8]21[O:15]CCO2)(=O)C.C[C:22]([CH3:24])=[O:23].N(CCO)(CCO)[CH2:26][CH2:27][OH:28]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:27]([O:23][CH2:22][CH2:24][CH:11]1[CH2:10][CH2:9][C:8](=[O:15])[CH:7]1[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:28])[CH3:26]

Participants

6

Reactant 3

HCID 180AcetoneHCID 7618TriethanolamineHCID 131710138HCID 131710138, compound

Product 1

HCID 53973838HCID 53973838, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 7.1 g of 2-acetoxyethyl-1,1-ethylenedioxy-2-n-pentyl-cyclopentane, 14.5 g of acetone and 0.0475 g of paratoluenesulphonic acid is brought to reflux during 1 hour. There is added thereto 0.08 mole of triethanolamine and the mixture is concentrated under reduced pressure on a water-bath. The residue is dissolved in 50 ml of benzene and washed with water until neutral. The distilled benzene solution yields 7 g of crude product which are rectified. There are obtained 5 g of 3-acetoxyethyl-2-n-pentyl-1-cyclopentanone (83.3% yield) having b.p.0.5 = 110°-113°C, nD15 = 1.4610.

Workup

  1. temperatureto reflux during 1 hour
  2. additionThere is added
  3. washwashed with water until neutral
  4. customThe distilled benzene solution yields 7 g of crude product which

Sources & evidence

ORD record
ord-2116449cf99042c9bd1a99e3e0b2fdd1
Source dataset
uspto-grants-1976_04
Patent number
US03951876

Reaction notes

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