Water → HCID 21523255, compound

HRID 918154Notes

Reaction equation

HRID 918154 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[C:10]([CH:12]([CH3:16])[CH2:13][CH2:14][OH:15])[CH:9]=[CH:8][C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[C:1]([O:15][CH2:14][CH2:13][CH:12]([C:10]1[CH:9]=[CH:8][C:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:6]([Cl:5])[CH:11]=1)[CH3:16])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21523261HCID 21523261, compound

Product 1

HCID 21523255HCID 21523255, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 3.92 gm (0.05 mol) of acetyl chloride in 20 ml of absolute toluene was allowed to flow into a solution of 10.0 gm (0.038 mol) of 3-(2-chloro-4-biphenylyl)-1-butanol and 5.0 gm (0.05 mol) of triethylamine in 100 ml of absolute toluene at room temperature; the resulting mixed solution was then stirred for several hours and was subsequently heated for 1 hour at 100°C. Thereafter, the reaction mixture was allowed to cool, water was then added, the toluene phase was separated, and the aqueous phase was extracted with ether. The combined organic solutions were washed until neutral, dried and evaporated, and the residue was distilled in vacuo, yielding 9.21 gm (80% of theory) of the desired ester in the form of a colorless oil having a boiling point of 145°-152°C at 0.06 mm Hg.

Workup

  1. additionthe resulting mixed solution
  2. temperatureto cool
  3. customthe toluene phase was separated
  4. extractionthe aqueous phase was extracted with ether
  5. washThe combined organic solutions were washed until neutral,
  6. customdried
  7. customevaporated
  8. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-6af8c1f814e14ac39450d77196192e6e
Source dataset
uspto-grants-1976_07
Patent number
US03969419

Reaction notes

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