HCID 10061046, compound → 1,2-Bis[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethanol

HRID 1588126Notes

Reaction equation

HRID 1588126 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].C([Li])(CC)C.[CH3:24][O:25][C:26]1[C:31]([O:32][CH2:33][O:34][CH3:35])=[CH:30][C:29]([O:36][CH3:37])=[C:28]([O:38][CH2:39][O:40][CH3:41])[C:27]=1[CH2:42][CH:43]=[O:44]>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[CH3:1][O:2][C:3]1[C:4]([O:15][CH2:16][O:17][CH3:18])=[CH:5][C:6]([O:13][CH3:14])=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:8]=1[CH:43]([OH:44])[CH2:42][C:27]1[C:28]([O:38][CH2:39][O:40][CH3:41])=[C:29]([O:36][CH3:37])[CH:30]=[C:31]([O:32][CH2:33][O:34][CH3:35])[C:26]=1[O:25][CH3:24]

Participants

6

Reactant 3

HCID 10061046HCID 10061046, compoundHCID 197572302-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehydeHCID 178418400CID 53628100

Product 1

HCID 197572131,2-Bis[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

351 Milligrams (1.36 mM) of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in a mixed solvent of 10 ml of tetrahydrofuran with 1 ml of hexamethylphosphoric triamide, and the solution was cooled to -78° C. in a dry ice-acetone bath. Then 1.60 ml (1.05M cyclohexane solution, 1.68 mM) of sec-butyllithium was added to the reaction mixture and stirred for 30 minutes. Next, a tetrahydrofuran solution containing 334 mg (1.11 mM) of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehyde in 2 ml of tetrahydrofuran was added thereto and stirred for 8 hours. The reaction mixture was concentrated under a reduced pressure, and the residue obtained was purified by a silica gel column chromatography (diameter 2 cm×length 10 cm, eluent: 40% ethyl acetate-n-hexane) to yield 503 mg of 1,2-bis[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethanol. Colorless oily substance.

Workup

  1. additionwas added
  2. stirringstirred for 8 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. customthe residue obtained
  5. customwas purified by a silica gel column chromatography (diameter 2 cm×length 10 cm, eluent: 40% ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-8348fc63632547ec908ab52539a2ca37
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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