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

HRID 26989Notes

Reaction equation

HRID 26989 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

HCID 887MethanolHCID 6212ChloroformHCID 13191832Ethyl (3R)-3,7-dimethyloctanoate

Product 1

HCID 13191833(R)-(+)-3,7-dimethyloctanoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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

  1. customHydrolysis
  2. customto give 207 mg

Sources & evidence

ORD record
ord-f2e143a40b584caaaa79a458e8751d79
Source dataset
uspto-grants-1979_04
Patent number
US04151360

Reaction notes

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