Pyridine → HCID 10469565, compound

HRID 2399052Notes

Reaction equation

HRID 2399052 reaction equation
[C:1]([C:4]1([CH3:18])[CH2:13][CH2:12][C:11]2[CH2:10][C:9]([OH:15])(C)[C:8]([CH3:16])=[C:7]([CH3:17])[C:6]=2[O:5]1)([OH:3])=[O:2].[C:19](OC(=O)C)(=[O:21])[CH3:20].N1C=CC=C[CH:27]=1>>[C:19]([O:15][C:9]1[C:10]([CH3:27])=[C:11]2[C:6](=[C:7]([CH3:17])[C:8]=1[CH3:16])[O:5][C:4]([C:1]([OH:3])=[O:2])([CH3:18])[CH2:13][CH2:12]2)(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86733193HCID 86733193, compound

Product 1

HCID 10469565HCID 10469565, compound

Procedure

To a partial solution of 5.0 g. (20 mmol) of (±)-2-carboxy-6-hydroxy-2,6,7,8-tetramethylchroman in 8.0 ml. of pyridine was added, dropwise over 10 minutes, 12.0 ml. of acetic anhydride. The solution was allowed to stand for 16 hours and was then worked up and dried by the procedure of Example 2 utilizing dichloromethane as a solvent to give a white solid. Crystallization from a mixture of ether-petroleum ether (b.p. 30- 60 degrees centigrade) gave (±)-6-acetoxy-2-carboxy-2,5,7,8-tetramethylchroman.

Workup

  1. dry with materialdried by the procedure of Example 2 utilizing dichloromethane as a solvent
  2. customto give a white solid
  3. customCrystallization
  4. additionfrom a mixture of ether-petroleum ether (b.p. 30- 60 degrees centigrade)

Sources & evidence

ORD record
ord-86ab84c790fc47b8b78c79d6a4ac0349
Source dataset
uspto-grants-1977_05
Patent number
US04026907

Reaction notes

Loading…