Diethyl Ether → HCID 21553993, compound

HRID 267747Notes

Reaction equation

HRID 267747 reaction equation
[CH:1]1[C:11]2[CH:10]([CH2:12][C:13](OCC)=O)[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+].CC[O:32]CC>>[CH:1]1[C:11]2[CH:10]([CH:12]([OH:32])[CH3:13])[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21553998HCID 21553998, compound

Product 1

HCID 21553993HCID 21553993, compound

Procedure

27 g. (0.096 mol) ethyl 6,11-dihydrodibenz[b,e]-oxepin-11-yl-acetate were added dropwise, with cooling, to a suspension of 3.8 g. (0.1 mol) lithium aluminum hydride in 300 ml. ether. The reaction mixture was subsequently stirred for 2 hours at ambient temperature, decomposed by the addition of a saturated aqueous solution of sodium chloride and the precipitated hydroxides were filtered off with suction and the filtrate was evaporated. The residue consisted of practically pure 6,11-dihydrodibenz[b,e]oxepin-11-yl-ethanol in a yield of 22.4 g. (97.5% of theory). 10 g. of this product were distilled in a high vacuum. There were obtained 9.0 g. of the product with a boiling point of 158° - 159°C./0.2 mm.Hg.

Workup

  1. temperaturewith cooling, to a suspension of 3.8 g
  2. filtrationthe precipitated hydroxides were filtered off with suction
  3. customthe filtrate was evaporated
  4. distillationof this product were distilled in a high vacuum
  5. customThere were obtained 9.0 g

Sources & evidence

ORD record
ord-aafabc7f23324a6aa2d8f45d604b5252
Source dataset
uspto-grants-1976_03
Patent number
US03944566

Reaction notes

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