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

HRID 2059288Notes

Reaction equation

HRID 2059288 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6]1([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:7]2=[O:12]>C(O)(=O)C.Br>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6]1([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:7]2=[O:12]

Participants

4

Reactant 1

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

Product 1

HCID 205469044'-Hydroxy-spiro(cyclohexane-1,2'-indan)-1'-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

5.6 g of 4'-methoxy-spiro(cyclohexane-1,2'-indan)-1'-one in 80 ml acetic acid and 20 ml 48% (w/w) aqueous hydrogen bromide are refluxed for 20 hours. The mixture is evaporated, diluted with water and extracted with ether. Evaporation of the solvent yields 4'-hydroxy-spiro(cyclohexane-1,2'-indan)-1'-one; M.Pt. 162°-164° (from ethanol).

Workup

  1. customThe mixture is evaporated
  2. additiondiluted with water
  3. extractionextracted with ether
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1dd032638e1043389ca7aed476d275f3
Source dataset
uspto-grants-1982_03
Patent number
US04322437

Reaction notes

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