Diethyl Ether → alpha,alpha-Diethyl-4-methyl-3-cyclohexene-1-methanol

HRID 1719837Notes

Reaction equation

HRID 1719837 reaction equation
[Mg].I[CH2:3][CH3:4].[CH3:5][C:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=O)[CH2:8][CH:7]=1.[CH2:15](OCC)[CH3:16]>>[CH2:15]([C:12]([CH2:3][CH3:4])([CH:9]1[CH2:10][CH2:11][C:6]([CH3:5])=[CH:7][CH2:8]1)[OH:14])[CH3:16]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 6340IodoethaneHCID 203504-Methyl-3-cyclohexene-1-carboxylic AcidHCID 5462224Magnesium

Product 1

HCID 13534004alpha,alpha-Diethyl-4-methyl-3-cyclohexene-1-methanol

Procedure

To 9.4 g of magnesium stirred in 350 ml of diethyl ether was added 60.4 g of iodoethane over 30 minutes to produce a mildly refluxing reaction mixture. The reaction mixture was refluxed for an additional hour, and then 23 g of the methyl ester of 4-methyl-3-cyclohexene-1-carboxylic acid in 20 ml of diethyl ether was added dropwise while maintaining gentle reflux. The reaction mixture was refluxed for an additional 1/2 hour, quenched with water, and extracted with diethyl ether; the ether extract was washed with saturated NaCl solution, dried (MgSO4), and stripped to yield an oil, which upon distillation gave 23.2 g of product, b.p. 90° C. (1 mm).

Workup

  1. customto produce
  2. temperaturea mildly refluxing
  3. customreaction mixture
  4. temperatureThe reaction mixture was refluxed for an additional hour
  5. temperaturewhile maintaining gentle reflux
  6. temperatureThe reaction mixture was refluxed for an additional 1/2 hour
  7. customquenched with water
  8. extractionextracted with diethyl ether
  9. extractionthe ether extract
  10. washwas washed with saturated NaCl solution
  11. dry with materialdried (MgSO4)
  12. customto yield an oil, which
  13. distillationupon distillation

Sources & evidence

ORD record
ord-f83ee87499804d35b624dd8a068e90f4
Source dataset
uspto-grants-1985_09
Patent number
US04542244

Reaction notes

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