Potassium Hydroxide → HCID 19595515, compound

HRID 612492Notes

Reaction equation

HRID 612492 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)([CH2:15][CH2:16][CH3:17])[CH2:10][C:11]([O:13]C)=[O:12])=[CH:5][CH:4]=1.O1CCOCC1.[OH-].[K+]>O>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)([CH2:15][CH2:16][CH3:17])[CH2:10][C:11]([OH:13])=[O:12])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 19595504HCID 19595504, compound

Product 1

HCID 19595515HCID 19595515, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 3,3-bis(4-methoxyphenyl)hexanoate (5.2 g, 15.2 mmol) was introduced into 20 ml of dioxane, KOH (1.05 g, 18.2 mmol) was added, and the mixture was boiled for about 1 h. It was subsequently diluted with water and washed with ethyl acetate, and the aqueous phase was then adjusted to pH 3 with dilute HCl and extracted with ethyl acetate. The organic phase was then washed with saturated NaCl solution, dried over MgSO4 and concentrated. Chromatography on silica gel (CH2Cl2 /methanol 3%) resulted in 4.1 g of a pale yellowish oil (84%).

Workup

  1. additionwas added
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was then washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8715097dfa104cedb015f073d966593b
Source dataset
uspto-grants-1999_12
Patent number
US06004988

Reaction notes

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