Sulfuric Acid → HCID 68734276, compound

HRID 341667Notes

Reaction equation

HRID 341667 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3([C:18]([CH3:20])([CH3:19])[O:17][C:12]4([CH2:16][CH2:15][CH2:14][CH2:13]4)[C:11]3=[O:21])[O:9]2)=[C:4]([CH2:22][CH3:23])[CH:3]=1.BrC1C=CC(C2C3(C(=O)C(C)(C)OC43CCCC4)O2)=C(CC)C=1.S(=O)(=O)(O)O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:11](=[O:21])[C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[O:17][C:18]([CH3:19])([CH3:20])[C:10]2=[O:9])=[C:4]([CH2:22][CH3:23])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 59562606HCID 59562606, compoundHCID 59562653HCID 59562653, compound

Product 1

HCID 68734276HCID 68734276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

To an ice cold solution of a mixture of 2-(4-bromo-2-ethylphenyl)-11,11-dimethyl-1,10-dioxadispiro[2.1.4.2]undecan-4-one and 2-(4-bromo-2-ethylphenyl)-10,10-dimethyl-1,9-dioxadispiro[2.0.4.3]undecan-11-one (7 g, 0.0185 mol) in dichloromethane (3.5 ml) is added concentrated sulphuric acid (21 ml), dropwise over 50-60 minutes, maintaining the temperature of the reaction mixture at 5-10° C. The reaction mixture is maintained at 5-10° C. for 10-15 minutes, quenched into crushed ice (100 g) and extracted with dichloromethane (3×75 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 9-(4-bromo-2-ethyl-phenyl)-7,7-dimethyl-6-oxaspiro[4.5]decane-8,10-dione (1.1 g) as a white solid.

Workup

  1. temperatureThe reaction mixture is maintained at 5-10° C. for 10-15 minutes
  2. customquenched
  3. custominto crushed ice (100 g)
  4. extractionextracted with dichloromethane (3×75 ml)
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe mixture is filtered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ebc0307da067417295aa54c5dded75c4
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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