Phosphoric Acid → 8-Methoxypsoralen

HRID 66074Notes

Reaction equation

HRID 66074 reaction equation
C(O[C:5]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:17])[O:12]2)=[CH:7][C:6]=1[CH2:18][CH:19]=[O:20])(=O)C.P(=O)(O)(O)O>>[CH3:16][O:15][C:14]1[C:13]2[O:12][C:11](=[O:17])[CH:10]=[CH:9][C:8]=2[CH:7]=[C:6]2[CH:18]=[CH:19][O:20][C:5]=12

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 537672567-Acetoxy-8-methoxycoumarin-6-acetaldehyde

Product 1

HCID 41148-Methoxypsoralen

Procedure

A solution of 2.76 g. (0.010 mole) of 7-acetoxy-8-methoxycoumarin-6-acetaldehyde in 30 ml. of 85% phosphoric acid was heated at 100° for 20 min, cooled and partitioned between water/methylene chloride. The aqueous phase was further extracted with methylene chloride. The organic extracts were combined, dried over sodium sulfate, and evaporated to yield 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one. Purification was achieved by filtration through a silica gel column, eluting with benzene/ethyl acetate, 4:1. The filtrate was evaporated to afford pure end product, mp 145°-146°.

Workup

  1. temperaturecooled
  2. custompartitioned between water/methylene chloride
  3. extractionThe aqueous phase was further extracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-93bfe99cd6aa459aaabfbd625861f881
Source dataset
uspto-grants-1978_12
Patent number
US04130568

Reaction notes

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