Hydrochloric Acid → HCID 86738149, compound

HRID 1659555Notes

Reaction equation

HRID 1659555 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:12]([CH3:13])[C:11]3[CH:14]=[C:15](/[CH:20]=[CH:21]/[CH3:22])[CH:16]=[C:17]([O:18][CH3:19])[C:10]=3[O:9]2)=[CH:4][C:3]=1[O:23][CH3:24].[CH2:25]=[O:26].Cl>[OH-].[K+]>[CH3:19][O:18][C:17]1[C:10]2[O:9][C@@H:8]([C:5]3[CH:4]=[C:3]([O:23][CH3:24])[C:2]([OH:1])=[C:7]([CH:6]=3)[CH2:25][OH:26])[C@H:12]([CH3:13])[C:11]=2[CH:14]=[C:15](/[CH:20]=[CH:21]/[CH3:22])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 6442393(-)-Licarin A

Product 1

HCID 86738149HCID 86738149, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

In a nitrogen atmosphere 10 g trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran are dissolved in 400 ml 2 N potash lye and treated with 37 ml 35 percent formalin solution, then held for 24 hours at 74° C. and treated twice within this period with the same amount of formaline solution. After cooling follows acidification with dilute hydrochloric acid until a pH of 1 is attained, then extraction with ether, washing of the ether phase with water, 5 percent NaHCO3 solution and water, and drying over Na2SO4. The oil remaining upon removal of the ether is crystallized from methylenechloride/petroleum ether (boiling point 60°-80° C.) and yields 7 g 5-[trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenylbenzofuran-2-yl]-2-hydroxy-3-methoxybenzyl alcohol, melting point 117°-119° C.

Workup

  1. temperatureAfter cooling
  2. extractionextraction with ether
  3. washwashing of the ether phase with water, 5 percent NaHCO3 solution and water
  4. dry with materialdrying over Na2SO4
  5. customThe oil remaining upon removal of the ether
  6. customis crystallized from methylenechloride/petroleum ether (boiling point 60°-80° C.)

Sources & evidence

ORD record
ord-3ca3167b96b149a0b4482bfbf79198fb
Source dataset
uspto-grants-1981_12
Patent number
US04304785

Reaction notes

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