Pyridine → HCID 18476677, compound

HRID 2187726Notes

Reaction equation

HRID 2187726 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][CH2:22][CH3:23].N1C=CC=CC=1>CN(C1C=CN=CC=1)C>[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][CH2:22][CH3:23])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18476681HCID 18476681, compound

Product 1

HCID 18476677HCID 18476677, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
55 °C

Procedure

6.1 g (60 mmol) of acetic anhydride are added dropwise to a solution of 10.6 g (50 mmol) of 4-hydroxy-3-propyl-biphenyl, 4.3 g (55 mmol) of pyridine and 0.1 g of 4-(N,N-dimethylamino)pyridine, and the mixture is heated at 50 to 60° C. for 2 hours. The reaction solution is left standing overnight at 20° C. and washed with water and dilute hydrochloric acid, and the organic phase is dried and concentrated. 11.4 g (yield: 89.8% of theory) of 4-acetoxy-3-propyl-biphenyl are obtained as a pale oil of log p=4.32 (pH=2.3).

Workup

  1. waitThe reaction solution is left
  2. washwashed with water and dilute hydrochloric acid
  3. customthe organic phase is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-17b4a34ab13e4232bb4ec8b05ba502a5
Source dataset
uspto-grants-2002_06
Patent number
US06410581B1

Reaction notes

Loading…