Ethyl bromoacetate → HCID 22814861, compound

HRID 848029Notes

Reaction equation

HRID 848029 reaction equation
[H-].[Na+].[C@@H:3]1([OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[OH:9].[H][H].[Na].Br[CH2:15][C:16](OCC)=[O:17]>C1(C)C=CC=CC=1.O>[O:9]1[C@@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@H:3]2[O:10][CH2:15][C:16]1=[O:17]

Participants

8

Reactant 5

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 92886trans-1,2-Cyclohexanediol2×HCID 5360545SodiumHCID 178418361HCID 178418361, compound

Product 1

HCID 22814861HCID 22814861, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a slurry of 54 grams of 55% sodium hydride in 1000 mls of toluene is portionwise added 140 grams of trans-1,2-cyclohexanediol at 90° C. with concommitant release of hydrogen. The resulting mass, containing the monosodium salt of trans-1,2-cyclohexanediol is stirred at 100° C. for 30 minutes. Ethyl bromoacetate (203 grams) is added dropwise to the stirred reaction mass at 100° C. over a 30 minute period. After stirring for 30 minutes, the mass is cooled to 20° C. Water (100 ml) is added and the organic layer is distilled to afford 130 grams of trans-hexahydro-1,4-benzodioxan-2-one. The product is purified by distillation through a 1"×12" Goodloe® packed column to afford a semi solid (m.p. 20°-22° C., bp. 97° C. at 1.2 mm).

Workup

  1. customat 90° C.
  2. stirringAfter stirring for 30 minutes
  3. temperaturethe mass is cooled to 20° C
  4. distillationthe organic layer is distilled

Sources & evidence

ORD record
ord-a557509c4fdd444fb640bc14c083d14e
Source dataset
uspto-grants-1981_10
Patent number
US04294266

Reaction notes

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