Methanol → (R)-(+)-3,7-dimethyloctanoic acid
Reaction equation
C([O:3][C:4](=[O:14])[CH2:5][C@H:6]([CH3:13])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])C.CO.C(Cl)(Cl)Cl>[OH-].[Na+]>[CH3:13][C@H:6]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][C:4]([OH:14])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrolysis: 400 mg. (2 mmol) of 3(R),7-dimethyl octanoic acid ethyl ester was refluxed in 6N NaOH (1 ml.) and methanol (4 ml.) for 2 hours. It was worked up as in Example 10 to give 207 mg. (60% yield) of 3(R),7-dimethyl octanoic acid (R-(+)-dihydrocitronellic acid), [α]D25 + 6.81° (c=5.039, CHCl3).
Workup
- customHydrolysis
- customto give 207 mg
Sources & evidence
- ORD record
- ord-98dffc58ad984a2d8ecaea506bc996e6
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04102909
Reaction notes
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