Thionyl Chloride → 5-(Chloromethyl)-2,3-dihydro-1h-indene

HRID 869854Notes

Reaction equation

HRID 869854 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14]O)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1>C(Cl)(Cl)Cl>[Cl:3][CH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 330183(2,3-dihydro-1H-inden-5-yl)methanol

Product 1

HCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indeneYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (120 ml, 1.65 mol) was added drop-wise to a rapidly stirred mixture of (2,3-dihydro-1H-inden-5-yl)methanol (81.4 g, 0.55 mol) in chloroform (500 ml) at 0° C. After the addition was complete, the resulting mixture was allowed to warm to room temperature and the stirring was continued for an additional 12 h. The chloroform was evaporated under reduced pressure to give a residue, that was purified by column chromatography (petroleum ether:ethyl acetate=15:1) to afford 5-(chloromethyl)-2,3-dihydro-1H-indene (90.5 g, 99%). 1H NMR (300 MHz, CDCl3) δ 2.06-2.19 (m, 4H), 2.93 (t, J=7.5, 4H), 4.54 (s, 2H), 7.15-7.31 (m, 3H).

Workup

  1. additionAfter the addition
  2. customThe chloroform was evaporated under reduced pressure
  3. customto give a residue, that
  4. customwas purified by column chromatography (petroleum ether:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-4a3756c987734f16ae59478bb5fb46b7
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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