Pyridine → HCID 18476675, compound

HRID 2187725Notes

Reaction equation

HRID 2187725 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[CH2:21][CH3:22].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[CH2:21][CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18476682HCID 18476682, compound

Product 1

HCID 18476675HCID 18476675, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.6 g (45 mmol) of acetic anhydride are added dropwise to a solution of 7.3 g (37 mmol) of 4-hydroxy-3-ethyl-biphenyl and 3.2 g (40 mmol) of pyridine in 60 ml of chloroform, and the mixture is boiled under reflux for 3 hours. The solution is allowed to cool and then washed with water and dilute hydrochloric acid and the organic phase is dried and concentrated. 8.0 g (yield: 90% of theory) of 4-acetoxy-3-ethyl-biphenyl are obtained as a very clear oil of log p=3.92 (pH=2.3).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureto cool
  3. washwashed with water and dilute hydrochloric acid
  4. customthe organic phase is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5dba90b0c996450e8125804bdd3a6986
Source dataset
uspto-grants-2002_06
Patent number
US06410581B1

Reaction notes

Loading…