Hydrochloric Acid → 2-(5-Hydroxypentyl)cyclopentanone 2-(5-acetoxypentyl)-cyclopentanone

HRID 1659003Notes

Reaction equation

HRID 1659003 reaction equation
CC([O:4][CH2:5][C:6]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][O:21][C:22]([CH3:24])=[O:23])=C2C=1C=CC=C2)=O.Cl>O>[OH:21][CH2:20][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH2:6][C:5]1=[O:4].[C:22]([O:21][CH2:20][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH2:6][C:5]1=[O:4])(=[O:23])[CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 867329372-(5-Hydroxypentyl)cyclopentanone 2-(5-acetoxypentyl)-cyclopentanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,500 g. (16.2 moles) of 2-(5-acetoxypentyl)-2-carbomethoxy/carboethoxy-cyclopentanone (Example 54), 2.2 l. of glacial acetic, 1 l. of concentrated hydrochloric acid, and 1 l. of water is refluxed for 18 hours, cooled, and partitioned between saturated brine and benzene. The organic phase is washed with saturated brine, dried (MgSO4), and evaporated in vacuo to yield 3155 g. of an oil.

Workup

  1. additionA mixture of 4,500 g
  2. temperaturecooled
  3. custompartitioned between saturated brine and benzene
  4. washThe organic phase is washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto yield 3155 g

Sources & evidence

ORD record
ord-3e04906fea2045c086540db3fad77fef
Source dataset
uspto-grants-1976_06
Patent number
US03966773

Reaction notes

Loading…