4-Hydroxybenzaldehyde → 1-(2,6-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

HRID 1278014Notes

Reaction equation

HRID 1278014 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[Na+].Cl>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH:10]=[CH:17][C:16]1[CH:19]=[CH:20][C:13]([OH:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 542816011-(2,6-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-oneYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7.6 grams (0.05 mole) of 2',6'-dihydroxyacetophenone and 6.1 gram (0.05 mole) p-hydroxybenzaldehyde in ethanol was added 100 ml. of 60% aqueous sodium hydroxide. The mixture was stirred at room temperature for 18 hours and then acidified with 6 N hydrochloric acid. The resulting orange solid was collected by filtration and washed with water. The solid was chromatographed on silica gel (200 g., 2.25 l., 20% acetone-Skellysolve "B") and 150 ml. fractions taken. Fractions 6-12 were combined and crystallized from methanol-methylene chloride giving fine orange needles, 28 g., m.p. 190°-192° C., resolidified and melted 210°-212° C., 22% yield).

Workup

  1. filtrationThe resulting orange solid was collected by filtration
  2. washwashed with water
  3. customThe solid was chromatographed on silica gel (200 g., 2.25 l., 20% acetone-Skellysolve "B") and 150 ml
  4. customcrystallized from methanol-methylene chloride giving fine orange needles, 28 g
  5. custommelted 210°-212° C.

Sources & evidence

ORD record
ord-05677965451349a08ea2cb0e2c805289
Source dataset
uspto-grants-1981_07
Patent number
US04279930

Reaction notes

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