P-Cresol → HCID 20097278, compound

HRID 1769808Notes

Reaction equation

HRID 1769808 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[CH:14]1[C:19](O)=[CH:18][CH:17]=[C:16]([CH3:21])[CH:15]=1>>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]1[C:18]2[C:19](=[CH:14][CH:15]=[C:16]([CH3:21])[CH:17]=2)[O:8][C:7](=[O:9])[CH2:6]1

Participants

3

Reactant 2

HCID 2879P-CresolHCID 268622-Propenoic acid, 3-(methoxyphenyl)-

Product 1

HCID 20097278HCID 20097278, compound

Procedure

A mixture of 2-methoxycinnamic acid (178 g, 1.0 mol), p-cresol (108 g, 1.0 mol), and p-touenesulphonic acid monohydrate (47.5 g, 0.25 mol) was stirred on a boiling water-bath for about 2 h during which time the system was evacuated with a waterpump to remove formed water. The solid was then broken up and washed copiously with water. The granular material was then stirred with a large volume of saturated NaHCO3 solution containing some 10% acetone. The product was filtered off, washed dried and recrystallised from acetone affording 167 g (62,5%) white crystals of the desired lactone, m.p. 140°.

Workup

  1. customwas evacuated with a waterpump
  2. customto remove
  3. customformed water
  4. washwashed copiously with water
  5. stirringThe granular material was then stirred with a large volume of saturated NaHCO3 solution
  6. additioncontaining some 10% acetone
  7. filtrationThe product was filtered off
  8. washwashed
  9. customdried
  10. customrecrystallised from acetone affording 167 g (62,5%) white crystals of the desired lactone, m.p. 140°

Sources & evidence

ORD record
ord-d4251b1fbe5045b9a758bdb31c3815af
Source dataset
uspto-grants-1995_01
Patent number
US05382600

Reaction notes

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