Hydrochloric Acid → HCID 12805671, compound

HRID 1462185Notes

Reaction equation

HRID 1462185 reaction equation
C[O:2][C:3]([CH2:5][CH:6]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=O.C([BH-](CC)CC)C.[Li+].Cl>O1CCCC1>[OH:2][CH2:3][CH2:5][CH:6]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12805670HCID 12805670, compoundHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 12805671HCID 12805671, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

33.7 g of 11-(methoxycarbonyl methyl) [dibenzo (b,e)-1,4-dioxepin] were added to 50 ml of tetrahydrofuran. This clear solution was cooled between 0° and 10° C. and one N solution of lithium triethylborohydride in tetrahydrofuran was very slowly added. This reactive solution was added for about 6 hours while the stirring and cooling were maintained. The mixture was then left between 0° and -5° C., and the excess of the reactive solution was hydrolyzed with 100 ml of a 3N hydrochloric acid solution. The tetrahydrofuran was evaporated. The residual aqueous phase was extracted thrice with isopropyl ether. The organic solutions were joined together, washed with hydrochloric acid and then water. The solvent was distilled off and there were obtained 32.2 g of 11-hydroxyethyl dibenzo (b,e)-1,4-dioxepin. This product recrystallized from the tetrahydrofuran gives 19.6 g of pure product (yield: 65%). The hydroxy ethyl compound distills at 160°-163° C. under 0.1 mmHg M.P.=62°-64° C. (M.K.).

Workup

  1. temperatureThis clear solution was cooled between 0° and 10° C.
  2. additionThis reactive solution was added for about 6 hours while the stirring and
  3. temperaturecooling
  4. temperaturewere maintained
  5. waitThe mixture was then left between 0° and -5° C.
  6. customThe tetrahydrofuran was evaporated
  7. extractionThe residual aqueous phase was extracted thrice with isopropyl ether
  8. washwashed with hydrochloric acid
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-b2d180c31fce440f8394cb396a0ec8d9
Source dataset
uspto-grants-1984_07
Patent number
US04459306

Reaction notes

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