Water → 1-(Methoxymethyl)-1H-indene

HRID 1703992Notes

Reaction equation

HRID 1703992 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C([Li])CCC.[CH3:15][O:16][CH2:17]Cl.O>CCOCC.CCCCCC>[CH3:15][O:16][CH2:17][CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 10326IndaneHCID 178418339Butyllithium

Product 1

HCID 136413801-(Methoxymethyl)-1H-indeneYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of indane (240 g) in dry ether (1 l) was slowly added, with stirring under a nitrogen atmosphere, 2.2 M solution (1 l) of n-butyllithium in n-hexane at -40° C over an hour. After 15 minutes, to this solution was added chloromethyl methyl ether (170 g) in dry ether (150 ml) under nitrogen at -55° C over 30 minutes. After stirring for another 30 minutes, water (1 l) was added with efficient stirring. The ether layer was separated, the aqueous phase extracted with ether (100 ml) twice, and the combined ether extract was washed with brine and dried over MgSO4. The ether was evaporated and the residual oily substance was distilled to give 1-methoxymethyl indene as yellow oil. (b.p. 50° C/0.2 mmHg, 258 g yield 78%)

Workup

  1. stirringAfter stirring for another 30 minutes
  2. customThe ether layer was separated
  3. extractionthe aqueous phase extracted with ether (100 ml) twice
  4. extractionthe combined ether extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. customThe ether was evaporated
  8. distillationthe residual oily substance was distilled

Sources & evidence

ORD record
ord-42ff5c4bc28848499c8ece4ca99ad98d
Source dataset
uspto-grants-1978_11
Patent number
US04125731

Reaction notes

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