Hydrochloric Acid → HCID 23665103, compound

HRID 2253963Notes

Reaction equation

HRID 2253963 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18][C:17]=2[CH:37]=1)[C:10]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-:41].[Na+:42].Cl.[OH2:44]>>[CH2:1]([O:8][CH:9]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18][C:17]=2[CH:37]=1)[C:10]([O-:44])=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+:42]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 15284465HCID 15284465, compound

Product 1

HCID 23665103HCID 23665103, compound

Procedure

A mixture of 2-benzyloxy-3-[2-(4-benzyloxybenzyl)-3,4-dihydro-2H-benzopyran-6-yl]propanenitrile (0.23 g, 0.47 mmol), ethanol (10 ml) and 6N sodium hydroxide (2 ml) was heated to reflux for 5 hours. Water (50 ml) was added and the solution was acidified with concentrated hydrochloric acid (2 ml), then extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated to an oil (0.19 g). The product was dissolved in methanol and treated with sodium methoxide (21 mg). The solvent was removed and the solid dried (7 mg, mp 165°-169° C.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to an oil (0.19 g)
  7. dissolutionThe product was dissolved in methanol
  8. additiontreated with sodium methoxide (21 mg)
  9. customThe solvent was removed
  10. customthe solid dried (7 mg, mp 165°-169° C.)

Sources & evidence

ORD record
ord-ef6404a41c654503ae12132ad9e86c2d
Source dataset
uspto-grants-1993_08
Patent number
US05232945

Reaction notes

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