Ammonium Chloride → HCID 20469274, compound

HRID 1388636Notes

Reaction equation

HRID 1388636 reaction equation
[CH3:1][C:2]1[CH:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]([CH3:13])[CH2:5][C:4](=[O:14])[CH:3]=1.[CH3:15][Li].[Cl-].[NH4+]>O1CCCC1>[CH3:15][C:4]1([OH:14])[CH2:5][CH:6]([CH3:13])[CH:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:2]([CH3:1])=[CH:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 936962-Cyclohexen-1-one, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-HCID 178418348HCID 178418348, compound

Product 1

HCID 20469274HCID 20469274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3,5-dimethyl-4-(3-methyl-2-butenyl)-2-cyclohexen-1-one (2.9 g, 0.015 mol), prepared according to Example 4, in anhydrous tetrahydrofuran (20 mL), was cooled to 0° C. under nitrogen and 1.6 M ethereal methyllithium (10 mL) added dropwise. The solution was allowed to warm to room temperature and stirred for 4 hours. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The ether extracts were washed with water, brine and dried (Na2SO4). Solvent removal and kugelrohr distillation (bath temperature 95°-100° C./0.1 mm) gave 2.8 g of the alcohol.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with ether
  3. washThe ether extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customSolvent removal and kugelrohr distillation (bath temperature 95°-100° C./0.1 mm)

Sources & evidence

ORD record
ord-1a4b8188c319418a8b634b2d0a1c3650
Source dataset
uspto-grants-1984_02
Patent number
US04432378

Reaction notes

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