Acetone → HCID 18431201, compound

HRID 840596Notes

Reaction equation

HRID 840596 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C(Cl)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:21]=[N+]=[N-].[Na+].C1(C)C=CC=CC=1.C[C:33](C)=[O:34]>O>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:21]=[C:33]=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1140TolueneHCID 33557Sodium AzideHCID 18431210HCID 18431210, compound

Product 1

HCID 18431201HCID 18431201, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 11-phenoxyundecanoyl chloride (31.1 g, 104.8 mmoles) in acetone (30 ml) was dropped into a solution of sodium azide (9.53 g, 146.6 mmoles) in water (30 ml), cooled in an ice bath, keeping the solution temperature between 10 and 15° C. After one hour, the solution was transferred in a separatory funnel and the lower phase (the aqueous one) was eliminated. The higher phase was transferred into a flask containing 100 ml of toluene, previously warmed at 65° C. After 1.5 hours, the solution was evaporated to dryness, giving 13.37 g of crude product, which could be used as such in the subsequent reaction.

Workup

  1. temperaturecooled in an ice bath
  2. customthe solution temperature between 10 and 15° C
  3. customthe solution was transferred in a separatory funnel
  4. customThe higher phase was transferred into a flask
  5. waitAfter 1.5 hours
  6. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-1225ca62985445e0a803bc33921235c4
Source dataset
uspto-grants-2002_04
Patent number
US06369073B1

Reaction notes

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