Resorcinol → HCID 13117147, compound

HRID 978618Notes

Reaction equation

HRID 978618 reaction equation
[CH2:1]([CH:4]1[C:8](O)([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3].[C:12]1([CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=1)[OH:13].O1CCCC1.C(N(CC)CC)C>O.C1(C)C=CC=CC=1>[CH2:1]([C:4]1[C:5](=[O:11])[CH2:6][CH:7]([O:13][C:12]2[CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=2)[C:8]=1[CH3:9])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13117147HCID 13117147, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Into the same flask as used in Example 1, 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (0.1 mol; 1 part), resorcinol (5 parts), tetrahydrofuran (1/2 part) and triethylamine (1/10 part) were charged, and the mixture was stirred at a temperature of 50° to 80° C. for 2 hours. After completion of the reaction, toluene (6 parts) and water (2 parts) were added thereto, and the separated organic layer was washed with a 5% aqueous solution of sodium carbonate. Toluene was evaporated off from the organic layer to give 2-allyl-3-methyl-4-(3-hydroxyphenoxy)-2-cyclopentenone. Yield, 95%. The product was purified by recrystallization from a mixture of chloroform and methanol (5:2 by volume). nD20 1.5707.

Workup

  1. additionwere charged
  2. additionwere added
  3. washthe separated organic layer was washed with a 5% aqueous solution of sodium carbonate
  4. customToluene was evaporated off from the organic layer

Sources & evidence

ORD record
ord-be9a450b2d6749ffbd4b2c09bedc2044
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

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