Pyridine → HCID 86734677, compound

HRID 328848Notes

Reaction equation

HRID 328848 reaction equation
[C:1]([C:4]1([CH3:18])[CH2:13][CH2:12][C:11]2[CH2:10][C:9]([OH:15])([CH3:14])[C:8](C)=[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([CH3:14])[CH:8]=[C:7]([CH3:17])[C:6]2[O:5][C:4]([C:1]([OH:3])=[O:2])([CH3:18])[CH2:13][CH2:12][C:11]=2[CH:10]1[CH3:27])(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86733193HCID 86733193, compound

Product 1

HCID 86734677HCID 86734677, 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° centigrade) gave (±)-6-acetoxy-2carboxy-2,5,6,8-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° centigrade)

Sources & evidence

ORD record
ord-c26cbae69fbc40e7b0c7c7c57d8f106e
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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