Sulfuric Acid → HCID 68730923, compound

HRID 341665Notes

Reaction equation

HRID 341665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3([C:14](=[O:15])[C:13]([CH2:17][O:18][CH3:19])([CH3:16])[O:12][C:11]3([CH3:21])[CH3:20])[O:9]2)=[C:4]([CH2:22][CH3:23])[CH:3]=1.BrC1C=CC(C2C3(C(=O)C(C)(C)OC3(COC)C)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:10](=[O:9])[C:11]([CH3:21])([CH3:20])[O:12][C:13]([CH2:17][O:18][CH3:19])([CH3:16])[C:14]2=[O:15])=[C:4]([CH2:22][CH3:23])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 59562589HCID 59562589, compoundHCID 59562610HCID 59562610, compound

Product 1

HCID 68730923HCID 68730923, 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)-6-methoxymethyl-4,4,6-trimethyl-1,5-dioxaspiro[2.4]heptan-7-one and 2-(4-bromo-2-ethylphenyl)-4-methoxymethyl-4,6,6-trimethyl-1,5-dioxaspiro[2.4]heptan-7-one (5 g, 0.013 mol) in dichloromethane (2.5 ml) is added concentrated sulphuric acid (15 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 (75 g) and extracted with dichloromethane (3×50 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 4-(4-bromo-2-ethylphenyl)-2-methoxymethyl-2,6,6-trimethylpyran-3,5-dione (1.82 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 (75 g)
  4. extractionextracted with dichloromethane (3×50 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-e992aa75d31e412495d03dc13559f0be
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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