Linalool → Linalyl acetoacetate

HRID 1870702Notes

Reaction equation

HRID 1870702 reaction equation
[CH2:1]=[CH:2][C:3]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])([CH3:5])[OH:4].[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1>CN(C)C1C=CN=CC=1>[O:17]=[C:13]([CH3:12])[CH2:14][C:15]([O:4][C:3]([CH3:5])([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH:2]=[CH2:1])=[O:16]

Participants

4

Reactant 2

HCID 6549LinaloolHCID 12661Diketene

Product 1

HCID 11791251Linalyl acetoacetateYield 92%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
55 °C

Procedure

A mixture of linalool (100 g, 0.648 mol) and 4-dimethylaminopyridine (0.40 g, 3.20 mmol) in a 500 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, addition funnel, magnetic stirrer and internal thermometer is heated to 55° C. Diketene (54.50 g, 0.648 mol) is added dropwise in the course of 30 min. The mixture has a slight exotherm and turns from yellow to red during this time. After stirring an additional hour at 50° C., the mixture is cooled to room temperature. At this point, NMR analysis indicates the reaction is complete. The material from this lot is carried onto the next step. Purification of an earlier sample from this route by flash chromatography (elution with dichloromethane) yields the desired product in 92% yield and nearly colorless.

Workup

  1. customfitted with a condenser, argon inlet, addition funnel, magnetic stirrer
  2. temperaturethe mixture is cooled to room temperature
  3. customPurification of an earlier sample from this route
  4. washby flash chromatography (elution with dichloromethane)

Sources & evidence

ORD record
ord-425a12a72893489fa1c29474defe2613
Source dataset
uspto-grants-2000_08
Patent number
US06100233

Reaction notes

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