Lithium Carbonate → HCID 67426523, compound

HRID 1174464Notes

Reaction equation

HRID 1174464 reaction equation
Br[CH:2]1[CH:17](Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9](=[O:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[Li+].[Li+]>CN(C)C=O>[C:9]1(=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 11125Lithium CarbonateHCID 59557679HCID 59557679, compound

Product 1

HCID 67426523HCID 67426523, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude 8,9-dibromocyclohexadecanone was fed into a reaction vessel containing a slurry of dimethylformamide (DMF) 700 ml and lithium carbonate (111 g 1.5 mole) at 150° C. The mass was aged for 14 hrs. The reaction was washed with 2 L water then 10% aqueous acetic acid (500 ml). Distillation over caustic (2% NaOH ) affords 54 g of 7,9-cyclohexadecadien-1-one and 86 g of a mixture of 8-cyclohexadecenone and 7,9-cyclohexadecadien-1-one.

Workup

  1. washThe reaction was washed with 2 L water
  2. distillationDistillation over caustic (2% NaOH )

Sources & evidence

ORD record
ord-c5a955b785884ec5af4ea83562e2ec4c
Source dataset
uspto-grants-2010_11
Patent number
US07838487B2

Reaction notes

Loading…