Hexane → HCID 12900455, compound

HRID 1106271Notes

Reaction equation

HRID 1106271 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14]CC=C)=[CH:9][C:10]=2[O:12][CH3:13])[O:5][C:4](=[O:18])[CH:3]=1.[CH3:19][CH2:20][CH2:21]CCC>CCN(C1C=CC=CC=1)CC>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:21][CH:20]=[CH2:19])[C:8]([OH:14])=[CH:9][C:10]=2[O:12][CH3:13])[O:5][C:4](=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 8058HexaneHCID 12900454HCID 12900454, compound

Product 1

HCID 12900455HCID 12900455, compound

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

A solution of 4-methyl-5-methoxy-7-allyloxycoumarin (XXXVI; 4.0 g) in diethylaniline (80 ml) was refluxed for 3 h. After cooling, n-hexane (400 ml) was added and the precipitate was collected, washed several times with n-hexane and crystallized twice from EtOAc to give 4-methyl-5-methoxy-7-hydroxy-8-allylcoumarin (XXXVII: 2.8 g; m.p. 198° C.) free from its isomer, the 4-methyl-5-methoxy-6-allyl-7-hydroxycoumarin (which during the successive steps can lead to the formation of a linear furocoumarin). ##STR40##

Workup

  1. temperatureAfter cooling
  2. customthe precipitate was collected
  3. washwashed several times with n-hexane
  4. customcrystallized twice from EtOAc

Sources & evidence

ORD record
ord-86754c414f9d4b2c97f1267772b8eb5b
Source dataset
uspto-grants-1982_01
Patent number
US04312883

Reaction notes

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