Sulfuric Acid → HCID 21163153, compound

HRID 1278264Notes

Reaction equation

HRID 1278264 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13](=[O:24])[CH:14]=[C:15]([CH:17](OCC)[O:18]CC)[O:16][C:11]=2[C:10]=1[CH2:27][CH2:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13](=[O:24])[CH:14]=[C:15]([CH:17]=[O:18])[O:16][C:11]=2[C:10]=1[CH2:27][CH2:28][CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21163168HCID 21163168, compound

Product 1

HCID 21163153HCID 21163153, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Benzyloxy-2-diethoxymethyl-8-propyl-4H-1-benzopyran-4-one (5.0 g) was dissolved in glacial acetic acid (50 ml), and 10% sulphuric acid (25 ml) was added. Steam was passed through the solution for 30 minutes. On cooling the yellow crystals which formed were filtered off, washed with light petroleum (bp 40°-60°), chromatographed on silica gel with ether, and then crystallised from ether to give the aldehyde (1.67 g), mp 150°.

Workup

  1. temperatureOn cooling the yellow crystals which
  2. customformed
  3. filtrationwere filtered off
  4. washwashed with light petroleum (bp 40°-60°)
  5. customchromatographed on silica gel with ether
  6. customcrystallised from ether

Sources & evidence

ORD record
ord-1fa8ebc191b9428fa7068cf99dee8ff2
Source dataset
uspto-grants-1981_07
Patent number
US04281008

Reaction notes

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