Chloride → 2-Methyl-2-phenylhexenol

HRID 544509Notes

Reaction equation

HRID 544509 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH2:4][C:5](=O)[CH2:6][CH3:7])[CH3:3].C(OC(=O)CC)(=[O:18])CC.[Cl-].C([Mg]Cl)C(C1C=CC=CC=1)(C)C>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH:4]=[CH:5][CH2:6][CH3:7])[CH2:3][OH:18]

Participants

7

Reactant 4

HCID 312ChlorideHCID 31263Propionic anhydride4×HCID 786393-Hexanone, 5-methyl-5-phenyl-HCID 178418740HCID 178418740, compound

Product 1

HCID 540912582-Methyl-2-phenylhexenol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A process for preparing 2-methyl-2-phenyl-4-hexanone having the structure: ##STR47## comprising the step of intimately admixing propionic anhydride having the structure: ##STR48## with neophymagnesium chloride having the structure: ##STR49## in the presence of an inert solvent selected from the group consisting of diethylether, toluene and tetrahydrufuran, the reaction taking place in the presence of or in the absence of a cuprous chloride catalyst; the mole ratio of propionic anhydride:neophylmagnesium chloride being from 0.5:1 up to about 2:1; the temperature of reaction being from -10° C. up to 0° C.; the concentration of propionic anhydride in solvent being from about 1 up to about 5 moles of propionic anhydride per liter of solvent; the time of addition of one reactant to the other varying from 0.5 hours up to 4 hours and the time of aging of the reaction mass being from 0.5 up to 4 hours.

Workup

  1. customthe temperature of reaction
  2. custombeing from -10° C. up to 0° C.
  3. additionthe time of addition of one reactant to the
  4. waitother varying from 0.5 hours up to 4 hours
  5. waitbeing from 0.5 up to 4 hours

Sources & evidence

ORD record
ord-99778318ba0c486382fd533fe8c46591
Source dataset
uspto-grants-1984_05
Patent number
US04450296

Reaction notes

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