Water → HCID 21289600, compound

HRID 868027Notes

Reaction equation

HRID 868027 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[CH2:11][CH:12]([CH3:14])[CH3:13].[CH3:15][CH2:16][O:17]CC.O>C(O)(=O)C.Br>[CH2:11]([C:4]1[C:5]([OH:9])=[C:6]([C:16](=[O:17])[CH3:15])[CH:7]=[CH:8][C:3]=1[OH:2])[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 10512023Benzene, 1,3-dimethoxy-2-(2-methylpropyl)-

Product 1

HCID 21289600HCID 21289600, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

1,3-Dimethoxy-2-(iso-butyl)benzene (11.3 g) was dissolved in acetic acid (250 ml) and 48% hydrobromic acid (150 ml). The resultant solution was heated to reflux for 2 days, cooled, and ether and water added. The ether layer was washed with brine (2×), dried over sodium sulfate, filtered and evaporated to dryness. The concentrate was chromatographed by HPLC (column eluted with a gradient of 1 to 10% ethyl acetate in hexane) to yield 3.87 g of the title product.

Workup

  1. temperatureto reflux for 2 days
  2. temperaturecooled
  3. washThe ether layer was washed with brine (2×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe concentrate was chromatographed by HPLC (column
  8. washeluted with a gradient of 1 to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-41dd007738324d39af91e9feb854bada
Source dataset
uspto-grants-1988_10
Patent number
US04777299

Reaction notes

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