Pyridine → HCID 20242348, compound

HRID 1719976Notes

Reaction equation

HRID 1719976 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:12])([CH3:11])[CH3:10])[CH2:5][CH2:4]1.[C:13](OC(=O)C)(=[O:15])[CH3:14].N1C=CC=CC=1>O>[C:13]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:12])([CH3:10])[CH3:11])[CH2:5][CH2:4]1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 20242346HCID 20242346, compound

Product 1

HCID 20242348HCID 20242348, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 258 g (1.5 M) of 7,8-dihydroxy-p-menthane, 2700 ml of acetic anhydride and 810 ml of pyridine was kept under stirring for 45 minutes, then it was poured onto ice (1 kg) and water (1000 ml). After its extraction with three fractions of 700 ml each of ether, the combined organic phases were washed with a 10% aqueous solution of NaOH (3×500 ml), water (2×500 ml) and a saturated aqueous solution of NaCl (500 ml). The solvent was evaporated and the residue (284 g) was distilled to give a colorless oil (276 g) having b.p. 108-110°/0.133 Pa (yield 86%).

Workup

  1. extractionAfter its extraction with three fractions of 700 ml each of ether
  2. washthe combined organic phases were washed with a 10% aqueous solution of NaOH (3×500 ml), water (2×500 ml)
  3. customThe solvent was evaporated
  4. distillationthe residue (284 g) was distilled

Sources & evidence

ORD record
ord-8d1ebf7ce4b245e6a6f4295a8cd30354
Source dataset
uspto-grants-1985_09
Patent number
US04543429

Reaction notes

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