Sodium Chloride → HCID 85551694, compound

HRID 231072Notes

Reaction equation

HRID 231072 reaction equation
[C:1]1([CH:7]2[CH2:13][CH2:12][C:11](=[O:14])[C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:23][N:24]=O)CCC.[Na].[Cl-].[Na+]>O1CCCC1.C(OCC)C.Cl>[OH:23][N:24]=[C:12]1[C:11](=[O:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13]1

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 142084352-Phenyl-3,4-dihydro-1-benzoxepin-5(2H)-oneHCID 86743195HCID 86743195, compound

Product 1

HCID 85551694HCID 85551694, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

5.36 g (22.5 m moles) of 2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin-5-one (compound R1 of Reference Example 1) was dissolved in a mixture of 130 ml of tetrahydrofuran and 230 ml of ethyl ether, and 13.4 ml of hydrogen chloride-saturated ethyl ether was added to the solution, which was then cooled to -20° C. 5.79 ml (49.5 m moles) of sodium butylnitrite was added dropwise to the solution, and the reaction mixture was allowed to stand at -15° C. to -20° C. for two days. A saturated sodium chloride aqueous solution was added to the reaction mixture to separate the phases. An organic phase was obtained, washed with water, and dried with anhydrous magnesium sulfate. After filtrating off the magnesium sulfate, the filtrate was concentrated, and the concentrate was washed with hexane and dried to obtain 5.46 g (yield 90.8%) of the desired compound.

Workup

  1. additionwas added to the solution, which
  2. customto separate the phases
  3. customAn organic phase was obtained
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationAfter filtrating off the magnesium sulfate
  7. concentrationthe filtrate was concentrated
  8. washthe concentrate was washed with hexane
  9. customdried

Sources & evidence

ORD record
ord-c9e84c581ad741e29aaec5a9a6196353
Source dataset
uspto-grants-1989_07
Patent number
US04845094

Reaction notes

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