Dibromomethane → HCID 13592052, compound

HRID 2350984Notes

Reaction equation

HRID 2350984 reaction equation
[OH:1][C:2]1[C:3]([CH3:14])=[C:4]([CH3:13])[C:5]2[O:9][C:8](=O)[S:7][C:6]=2[C:11]=1[CH3:12].[CH:15]([O:17][CH2:18][CH3:19])=[CH2:16].C(Br)Br.C(=O)(O)[O-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CS(O)(=O)=O.O>[CH2:15]([O:17][CH:18]([O:1][C:2]1[C:3]([CH3:14])=[C:4]([CH3:13])[C:5]2[O:9][CH2:8][S:7][C:6]=2[C:11]=1[CH3:12])[CH3:19])[CH3:16]

Participants

8

Reactant 4

HCID 3024Dibromomethane2×HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 130893525-Hydroxy-4,6,7-trimethyl-2H-1,3-benzoxathiol-2-one

Product 1

HCID 13592052HCID 13592052, compound

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidCatalystHCID 21218Trioctylmethylammonium chlorideCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 7.35 g of 5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-one, 20 ml of ethyl vinyl ether and 20 ml of methylene dibromide was cooled down to -20° C. under a stream of nitrogen, and then 20 mg of methanesulfonic acid were added dropwise, while stirring. After completion of the dropwise addition, the reaction temperature was gradually raised to room temperature, and the mixture was stirred for 3 hours at room temperature. To this reaction mixture were added 30 ml of water, 8.8 g of sodium bicarbonate and 1.0 g of Aliquat 336 (a trade mark for methyltrioctylammonium chloride), and the mixture was heated under reflux for 9 hours, which caused the excess methylene dibromide to vaporize gradually and leave a crude oil. This crude oil was extracted with diethyl ether, and the extract was dried over anhydrous sodium sulfate. The ether was then distilled off, to yield 12 g of an oily substance, which was purified by silica gel column chromatography. From the portion which could be eluted with a 20:1 by volume mixture of petroleum ether and diethyl ether were obtained 5.2 g of the title compound melting at 52°-54° C.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe reaction temperature was gradually raised to room temperature
  3. stirringthe mixture was stirred for 3 hours at room temperature
  4. temperaturewas heated
  5. temperatureunder reflux for 9 hours
  6. customleave a crude oil
  7. extractionThis crude oil was extracted with diethyl ether
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. distillationThe ether was then distilled off
  10. customto yield 12 g of an oily substance, which
  11. customwas purified by silica gel column chromatography
  12. washFrom the portion which could be eluted with a 20:1 by volume mixture of petroleum ether

Sources & evidence

ORD record
ord-86c1e0c8a26649409d734d56d50211ed
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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