Pyridine → HCID 10469565, compound

HRID 268412Notes

Reaction equation

HRID 268412 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°C.) 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°C.)

Sources & evidence

ORD record
ord-063aff2b7901419fa5f7b22abac4b822
Source dataset
uspto-grants-1976_03
Patent number
US03947473

Reaction notes

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