Acetic Anhydride → HCID 10469565, compound

HRID 1755601Notes

Reaction equation

HRID 1755601 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:6][CH2:5]2.[CH3:19][C:20](OC(C)=O)=[O:21]>N1C=CC=CC=1>[C:20]([O:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:6][CH2:5]2)(=[O:21])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 40634Trolox

Product 1

HCID 10469565HCID 10469565, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (5.0 g, 19.99 mmol) was dissolved in pyridine (18 mL) and Ac2O added (10 mL) in one portion. The exothermic reaction warmed to 40° C., was let cool to room temperature and stirred overnight. The crude reaction mixture was quenched with 100 mL H2O, stirred for 1 h followed by additional 100 mL H2O and 1 h of stirring. A fine white precipitate of 6-acetoxy-2,5,7,8-tetramethylchroman-2-carboxylic acid was formed and collected by filtration (4.544 g).

Workup

  1. customThe exothermic reaction
  2. temperaturewas let cool to room temperature
  3. customThe crude reaction mixture
  4. customwas quenched with 100 mL H2O
  5. stirringstirred for 1 h
  6. customfollowed by additional 100 mL H2O and 1 h
  7. stirringof stirring

Sources & evidence

ORD record
ord-3347b1eb1ae646d084e34ef83a03844b
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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