Water → HCID 67444125, compound

HRID 1666556Notes

Reaction equation

HRID 1666556 reaction equation
CC(C[Al]CC(C)C)C.C([O:12][C:13](=O)[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])C.O>C1COCC1>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([CH:15]=[CH:14][CH2:13][OH:12])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16682954DibahHCID 67443097HCID 67443097, compound

Product 1

HCID 67444125HCID 67444125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

Dibal-H (0.0255 mol) was added at −35° C. to a mixture of 3-(4-methyl-2-nitro-phenyl)-acrylic acid ethyl ester (0.0085 mol) in THF (80 ml) under N2 flow. The mixture was stirred at −35° C. for 15 minutes. H2O (20 ml) was added drop wise at −35° C. under N2 flow. The mixture was half-evaporated. CH2Cl2 was added. The mixture was filtered over celite. Celite was washed with CH2Cl2. The filtrate was washed with H2O. The organic layer was separated, dried (over MgSO4), filtered and the solvent was evaporated. Yield: 2 g of 3-(4-Methyl-2-nitro-phenyl)-prop-2-en-1-ol (e-2) (100%).

Workup

  1. customThe mixture was half-evaporated
  2. additionCH2Cl2 was added
  3. filtrationThe mixture was filtered over celite
  4. washCelite was washed with CH2Cl2
  5. washThe filtrate was washed with H2O
  6. customThe organic layer was separated
  7. dry with materialdried (over MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5622655a132c4989bb210fdeb5eec125
Source dataset
uspto-grants-2011_10
Patent number
US08044073B2

Reaction notes

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