Methanol → (R)-(+)-3,7-dimethyloctanoic acid

HRID 26990Notes

Reaction equation

HRID 26990 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>[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

4

Reactant 2

HCID 887MethanolHCID 13191832Ethyl (3R)-3,7-dimethyloctanoate

Product 1

HCID 13191833(R)-(+)-3,7-dimethyloctanoic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

300 mg. of 3(R),7-dimethyl octanoic acid ethyl ester obtained from example 14 was refluxed in 6 N NaOH (1 ml.), methanol (4 ml.) for 2 hours. It was worked up as in Example 10 to give 226 mg. (87.5% yield) of R-(+)-dihydrocitronellic acid, b.p. 54°/0.4 mmHg. (Kugelrohr), [α]D25 +6.31° (c=5.069, CHCl3).

Workup

  1. customto give 226 mg

Sources & evidence

ORD record
ord-76e53e5eab304588b192d0a43b595f39
Source dataset
uspto-grants-1979_04
Patent number
US04151360

Reaction notes

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