Pyridine → (+/-)-(6-Acetoxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid

HRID 268407Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][C:16]([OH:18])=[O:17])([CH3:14])[CH2:6][CH2:5]2.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C([O-])(O)=O.[Na+]>O1CCCC1.O>[C:26]([O:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][C:16]([OH:18])=[O:17])([CH3:14])[CH2:6][CH2:5]2)(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 66.1 g. (0.25 mol.) of (±)-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid and 250 ml. each of pyridine and acetic anhydride was stirred at 25°C. under N2 for 20 hours and stripped of solvent at 40°C. to give an orangebrown oil. To a suspension of this material in 500 ml. of H2O and 100 ml. of tetrahydrofuran was added 166 g. (2.0 mol.) of NaHCO3. The suspension was stirred at 25°C. for 4.0 hours, washed with ether, acidified with 2N-aqueous HCl and extracted with ether. The ether solutions were washed with saturated brine, dried over sodium sulfate and stripped of solvent to give (±)-(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid as an orangeish resin. Crystallization from diethyl ether petroleum ether (b.p. 30°-60°C.) gave (±)-(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid as a granular white solid.

Workup

additionA mixture of 66.1 g
customstripped of solvent at 40°C.
customto give an orangebrown oil
additionTo a suspension of this material in 500 ml
washwashed with ether
extractionextracted with ether
washThe ether solutions were washed with saturated brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-f7f0f9db3dc94978bb17d53c47a16c90
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947473

Reaction notes

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