Water → HCID 68542744, compound

HRID 2241833Notes

Reaction equation

HRID 2241833 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.COC1C=CC(C[O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[O:29][C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([C:38]([F:41])([F:40])[F:39])[CH:31]=2)=CC=1.C(Cl)Cl.O>CC(=O)OCC>[OH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([C:38]([F:39])([F:40])[F:41])[CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68547016HCID 68547016, compound

Product 1

HCID 68542744HCID 68542744, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2,3,-Dichloro-5,6-dicyano-1,4-benzoquinone (hereinafter “DDQ) (18.2 g, 80.2 mmol) was added to a solution of 4-[2-(4-methoxy-benzyloxy)cyclohexyloxy]-2-trifluoromethyl-benzonitrile (17.77 g, 43.83 mmol), methylene chloride (500 mL) and water (50 mL). The reaction was allowed to stir at room temperature for 3 days. A solid formed and was filtered off. The resulting filtrate was passed through a silica plug and condensed under reduced pressure. A column was run using a gradient of 17-80% EA in Hexanes. A second column was run using 4:1 Hex:EA. This yielded the desired product, 4-(2-hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile (4.0 g, 32% yield).

Workup

  1. customA solid formed
  2. filtrationwas filtered off
  3. customThe resulting filtrate was passed through a silica plug and condensed under reduced pressure

Sources & evidence

ORD record
ord-a9c9117551484844811964b253fd5e4c
Source dataset
uspto-grants-2010_03
Patent number
US07670613B2

Reaction notes

Loading…