Hydrochloric Acid → HCID 85613053, compound

HRID 1602741Notes

Reaction equation

HRID 1602741 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[O:14][C:13](=O)[C:12]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>C1(C)C=CC=CC=1.O1CCCC1>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[O:14][CH2:13][C:12]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14241908HCID 14241908, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 85613053HCID 85613053, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Acetoxyphenyl)-7-methoxy-3-phenyl-coumarin (180 g) was dissolved in toluene (2.1 l) at 70° C. and added to a suspension of lithium aluminium hydride (35.4 g) in tetrahydrofuran (2.1 l). The reaction mixture was kept below 60° C. during the addition. The reaction mixture was cooled down to room temperature. Water (45 ml) was carefully added and then 5M hydrochloric acid (1.2 l). The mixture was heated to 60-65° C. and stirred at for 3 hours. The organic phase was separated. The aqueous phase was extracted with toluene (250 ml). The combined organic phase was washed with water (250 ml) and evaporated to an oil. The oil was dissolved in boiling ethanol (600 ml). The solution was cooled and water was slowly added (400 ml) and the mixture was seeded. The crystals were filtered off, washed with water/ethanol; 25/75 (200 ml) and dried.

Workup

  1. additionThe reaction mixture was kept below 60° C. during the addition
  2. temperatureThe mixture was heated to 60-65° C.
  3. customThe organic phase was separated
  4. extractionThe aqueous phase was extracted with toluene (250 ml)
  5. washThe combined organic phase was washed with water (250 ml)
  6. customevaporated to an oil
  7. dissolutionThe oil was dissolved
  8. temperatureThe solution was cooled
  9. additionwater was slowly added (400 ml)
  10. filtrationThe crystals were filtered off
  11. washwashed with water/ethanol
  12. dry with material25/75 (200 ml) and dried

Sources & evidence

ORD record
ord-86727739bb0b46d0bbde6176deac197b
Source dataset
uspto-grants-1999_11
Patent number
US05985306

Reaction notes

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