Ethanol → HCID 21163198, compound

HRID 1278284Notes

Reaction equation

HRID 1278284 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][CH:7]([C:12](Cl)=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1.[CH2:17]([OH:19])[CH3:18].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][CH:7]([C:12]([O:19][CH2:17][CH3:18])=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 53901959HCID 53901959, compound

Product 1

HCID 21163198HCID 21163198, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 9.4 g of 6-chloro-4,4-dimethyl-[4H]-1,3-benzodioxin-2-carboxylic acid chloride in 50 ml of anhydrous benzene was added dropwise at room temperature with stirring to a mixture of 2.3 g of ethanol, 30 ml of anhydrous benzene and 3.03 g of triethylamine and the solution was stirred for 6 hours at room temperature and was vacuum filtered. The filtrate was washed with 70 ml of an aqueous saturated sodium bicarbonate solution and twice with 70 ml of water, was dried over magnesium sulfate, treated with activated carbon and filtered. The filtrate was evaporated to dryness under reduced pressure and the 8.4 g of residue were chromatographed over silica gel H. Fractional elution with methylene chloride and evaporation of the solvent yielded 5.3 g of ethyl 6-chloro-4,4-dimethyl-[4H]-1,3-benzodioxin-2-carboxylate in the form of an oil which crystallized at less than 50° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 70 ml of an aqueous saturated sodium bicarbonate solution and twice with 70 ml of water
  3. dry with materialwas dried over magnesium sulfate
  4. additiontreated with activated carbon
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customthe 8.4 g of residue were chromatographed over silica gel H
  8. washFractional elution
  9. customwith methylene chloride and evaporation of the solvent

Sources & evidence

ORD record
ord-f6b9ec75b6834ee9954f73dbf8f0bd51
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

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