Indene → HCID 131713525, compound

HRID 1262681Notes

Reaction equation

HRID 1262681 reaction equation
[Cl:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1>>[Cl:1][C:2]1[C:3]2[O:10][C@@H:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][C@@H:12]3[CH2:5][C:4]=2[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 7219IndeneHCID 130597302-Chloro-6-(hydroxymethyl)phenol

Product 1

HCID 131713525HCID 131713525, compound

Procedure

3-Chloro-2-hydroxybenzyl alcohol (20.0 g) (prepared by the method of Zincke, Hanus and Ziegler, J.Prakt. Chem., (2), 152 126(1939)), and indene (15 ml) were heated together at 190°-200° for 2.5 hr. The crude product was chromatographed on silica gel, eluting with toluene/60°-80° petroleum ether to yield a colourless oil (2.34 g) which was distilled in vacuo to give an oil which crystallised on standing (1.70 g., b.pt. 115°-120°/0.05 mmHg m.pt. 60°-63°). The recrystallised product, from ethanol was identified, by 1H-n.m.r., as cis-6-chloro-4b,10,10a,11-tetrahydrobenz(b)indeno(2,1-e) pyran, (1.20 g., m.pt-63°-65°).

Workup

  1. customThe crude product was chromatographed on silica gel
  2. washeluting with toluene/60°-80° petroleum ether

Sources & evidence

ORD record
ord-7ba24253aa904af898df243871292f02
Source dataset
uspto-grants-1984_06
Patent number
US04452991

Reaction notes

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