4-Hydroxyindan → HCID 12531905, compound

HRID 1704059Notes

Reaction equation

HRID 1704059 reaction equation
[CH2:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH2:3][CH2:2]1.C[O-].[Na+].[O-2].[K+].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>CO.C1C=CC=CC=1.O>[CH2:1]1[C:9]2[C:4](=[C:5]([O:10][CH:18]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=4)=[CH:25][CH:24]=3)[C:19]([O:21][CH3:22])=[O:20])[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 742334-HydroxyindanHCID 9989219Potassium oxideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531905HCID 12531905, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.36 g of 4-indanol, 1.188 g of sodium methoxide and 50 mg of potassium oxide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed overnight and then poured into 100 ml of water. The mixture is extracted with 2 × 75 ml of ether. The combined extracts are washed with 50 ml of 5% NaOH, 50 ml of water, 50 ml saturated brine, and dried (MgSO4). Evaporation of the solvent yields a yellow oil. Chromatography on 100 g of silica gel (benzene, 400 ml) yields the product as a light yellow oil which solidifies on standing.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. extractionThe mixture is extracted with 2 × 75 ml of ether
  3. washThe combined extracts are washed with 50 ml of 5% NaOH, 50 ml of water, 50 ml saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customyields a yellow oil

Sources & evidence

ORD record
ord-04fd0bb659aa444ea8ab46141eae9416
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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