Hydrochloric Acid → 4'-Methoxy-spiro(cyclohexane-1,2'-indan)-1'-one

HRID 2059287Notes

Reaction equation

HRID 2059287 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.O.Cl>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6]1([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:7]2=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 81001,5-DibromopentaneHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 205469054'-Methoxy-spiro(cyclohexane-1,2'-indan)-1'-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 20 g 4-methoxyindan-1-one and 24 g 1,5-dibromopentane in 150 ml benzene is added quickly dropwise to a solution of potassium tert.-butylate (produced from 9.7 g potassium and excess tert.-butanol) in 200 ml benzene at 80°. The mixture is refluxed for 4 hours, treated with 50 ml water and 200 ml 2 N hydrochloric acid, and extracted with benzene. Chromatography on silicagel of the benzene phase gives 4'-methoxy-spiro(cyclohexane-1,2'-indan)-1'-one. M.Pt. 94°-96°.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. extractionextracted with benzene

Sources & evidence

ORD record
ord-c392416097b74e16bb514268b693b65e
Source dataset
uspto-grants-1982_03
Patent number
US04322437

Reaction notes

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