Water → HCID 54046372, compound

HRID 1074647Notes

Reaction equation

HRID 1074647 reaction equation
[C:1]([C:4]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:16][Mg]Cl.O>O1CCCC1>[CH3:2][C:1]([CH3:16])([C:4]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1)[OH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 1090051-(1-Cyclododecen-1-yl)ethanoneHCID 178418332HCID 178418332, compound

Product 1

HCID 54046372HCID 54046372, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

52 g (0.25 mole) of 1-acetyl-1-cyclododecene, prepared as described in Example 2, are added over 30 minutes to 200 ml of a 1.5-molar solution of methyl-magnesium chloride in tetrahydrofuran at from 0° to +10° C. After completion of the addition, the reaction mixture is hydrolyzed with 20 ml of water and the tetrahydrofuran solution is filtered to remove the salt which has precipitated. After destilling off the tetrahydrofuran under reduced pressure (50° C./20 mbars) the product which remains is fractionated. 52 g of dimethyl-cyclododecenyl-carbinol (96% yield) of boiling point=108°-112° C./0.01 mm Hg and refractive index nD25 =1.5000 are obtained.

Workup

  1. additionAfter completion of the addition
  2. filtrationthe tetrahydrofuran solution is filtered
  3. customto remove the salt which
  4. customhas precipitated
  5. customunder reduced pressure (50° C./20 mbars)

Sources & evidence

ORD record
ord-755ca918e2e0460e9c573fe8196f2e3d
Source dataset
uspto-grants-1983_07
Patent number
US04393245

Reaction notes

Loading…