Water → HCID 12531870, compound

HRID 1863334Notes

Reaction equation

HRID 1863334 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:8]([OH:14])=[CH:7][CH:6]=1.Br[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18].O>CO.C1C=CC=CC=1.[I-].[K+]>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH:16]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[CH:23][CH:22]=2)[C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:13]=1[CH2:12][CH2:11][CH2:10]2

Participants

8

Reactant 4

HCID 962WaterHCID 8961ChlorindanolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531870HCID 12531870, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 1.19 g of sodium methoxide, 4.22 g of 7-chloro-4-indanol, and 100 mg of potassium iodide in 40 ml of methanol was added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture was heated at reflux overnight, cooled, and then poured into 100 ml of water. The mixture was extracted with 2×75 ml of ether. The combined extracts were washed with 2×50 ml of 5% NaOH, 2×50 ml water, 50 ml saturated brine, and dried (MgSO4). Evaporation of the solvent yielded a yellow oil which solidified on trituration with petroleum ether to yield 7.14 g of product as a cream colored solid, mp 94°-96° C. The solid was taken up in 75 ml of hot hexane, decanted away from a small amount of oil, and the supernatant liquid cooled to yield 5 g of a cream colored crystal, mp 97°-98.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. extractionThe mixture was extracted with 2×75 ml of ether
  5. washThe combined extracts were washed with 2×50 ml of 5% NaOH, 2×50 ml water, 50 ml saturated brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customyielded a yellow oil which

Sources & evidence

ORD record
ord-6a9bb6e6521843a3a23dca2eff46f9c5
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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