4-Hydroxy-5-methoxy-1-indanone → 2,3-dihydro-5-methoxy-1H-inden-4-ol

HRID 2185638Notes

Reaction equation

HRID 2185638 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O>Cl.O.[Zn]>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:7]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:2]=1[OH:1]

Participants

5

Reactant 1

HCID 112638284-Hydroxy-5-methoxy-1-indanone

Product 1

HCID 110082602,3-dihydro-5-methoxy-1H-inden-4-olYield 79.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The 20.5 g of 2,3-dihydro4-hydroxy-5-methoxy-1H-inden-1-one were suspended in a mixture of 310 ml of concentrated aqueous hydrochloric acid and 53 ml of water. Freshly prepared zinc amalgame (from 87 g of zinc wool) was added and the mixture was stirred for 3 hours at ambient temperature. After decantation the resting zinc amalgame was washed three times with diethyl ether and the acidic water solution was extracted with diethyl ether. The combined ether solutions were washed with a 1N aqueous hydrochloric acid solution, dried over magnesium sulfate, filtered and evaporated in vacuo to afford 15.0 g of 2,3-dihydro-5-methoxy-1H-inden-4-ol, M.S. (C.I.) (M/Z): 165 [M+H]+.

Workup

  1. washAfter decantation the resting zinc amalgame was washed three times with diethyl ether
  2. extractionthe acidic water solution was extracted with diethyl ether
  3. washThe combined ether solutions were washed with a 1N aqueous hydrochloric acid solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-bec2e54b70554a819b0a488cf04d5fad
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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