1-Octene, 7-methoxy-3,7-dimethyl- → HCID 70498408, compound

HRID 1980009Notes

Reaction equation

HRID 1980009 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[CH3:6][O:7][C:8]([CH3:17])(C)[CH2:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH:13]=[CH2:14]>O1CCCC1.[Cl-].[Cl-].C1([Ti+2]C2C=CC=C2)C=CC=C1>[CH3:17][C:8]1([O:7][CH3:6])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]1[CH2:14][CH2:3][CH2:2][CH2:1][CH2:17][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH3:13]

Participants

5

Reactant 2

HCID 1038251-Octene, 7-methoxy-3,7-dimethyl-HCID 178455851HCID 178455851, compound

Product 1

HCID 70498408HCID 70498408, compound

Reagents, catalysts & solvents 2

HCID 178420582HCID 178420582, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-propylmagnesium bromide (0.25 mole) in tetrahydrofuran (200 ml) was added 7-methoxy-3,7-dimethyl-1-octene (42.5 g) and biscyclopentadienyl titanium dichloride (1.25 g). After the vigorous reaction subsided, the mixture was heated in an oil bath (75°) for 19 hours. Aliquot quench at this point indicated ~50% conversion. The Grignard exchange product was transferred to a separatory funnel, and added dropwise to p-isopropylbenzyl chloride (21 g) in THF (300 ml) containing cuprous chloride (2.5 g) cooled at 0° to -10° while stirring. On warming to room temperature overnight, the reaction was then quenched with aqueous ammonium chloride and extracted with pentane. The pentane extracts were distilled to give product (2,6-dimethyl-2-methoxy-9-isopropylphenylnonane) (12.5 g; bp 150°-152° /0.25-0.3 torr) contaminated with some p, p'-diisopropylbibenzyl.

Workup

  1. customAfter the vigorous reaction
  2. temperaturethe mixture was heated in an oil bath (75°) for 19 hours
  3. customAliquot quench at this point
  4. customThe Grignard exchange product was transferred to a separatory funnel
  5. additionadded dropwise to p-isopropylbenzyl chloride (21 g) in THF (300 ml)
  6. additioncontaining cuprous chloride (2.5 g)
  7. temperaturecooled at 0° to -10°
  8. customthe reaction was then quenched with aqueous ammonium chloride
  9. extractionextracted with pentane
  10. distillationThe pentane extracts were distilled

Sources & evidence

ORD record
ord-f1c3549cd42f4e13ae80c94ccdb23f7b
Source dataset
uspto-grants-1984_11
Patent number
US04484007

Reaction notes

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