Water → HCID 54424346, compound

HRID 1275958Notes

Reaction equation

HRID 1275958 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH3:8][C:9]1([CH3:21])[C:13]([CH3:14])=[CH:12][CH2:11][CH:10]1[CH:15]=[CH:16][CH2:17]C(O)C.O>CN(C)C1C=CN=CC=1.CC(OC)(C)C>[CH3:8][C:9]1([CH3:21])[C:13]([CH3:14])=[CH:12][CH2:11][CH:10]1[CH:15]=[CH:16][CH2:17][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1068064-Penten-2-ol, 5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-

Product 1

HCID 54424346HCID 54424346, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
52.5 °C

Procedure

50 g (0.48 mol) of acetic anhydride was added dropwise to the solution of 78.6 g (0.40 mol) of 5-(2,2,3-trimethylcyclopent-3-enyl)pent-4-en-2-ol and 5.0 g of 4-dimethylaminopyridine in 150 ml of MTBE. The reaction mixture was stirred at 50-55° C. for 1 hour, treated with 0.5 l of water and extracted with 3×150 ml of hexane. The combined organic layers were neutralized with aqueous potassium hydrogen carbonate solution, washed with water, dried (MgSO4) and evaporated in vacuo. The residue (102 g) was distilled at 80-81° C./0.2 Torr to give 89.8 g (95% yield) of acetic acid 5-(2,2,3-trimethyl-cyclopent-3-enyl)pent-4-en-2-yl ester.

Workup

  1. extractionextracted with 3×150 ml of hexane
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. distillationThe residue (102 g) was distilled at 80-81° C./0.2 Torr

Sources & evidence

ORD record
ord-fbb6b26b32e7453b976a3feb223574f0
Source dataset
uspto-grants-2000_12
Patent number
US06162954

Reaction notes

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