Salicyl Alcohol → HCID 86739458, compound

HRID 1262679Notes

Reaction equation

HRID 1262679 reaction equation
O[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1>>[CH:9]1[CH:8]=[CH:7][CH:6]=[C:3]2[C:2]=1[CH2:10][C@H:11]1[C@@H:4]2[O:5][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12]1

Participants

3

Reactant 2

HCID 5146Salicyl AlcoholHCID 7219Indene

Product 1

HCID 86739458HCID 86739458, compound

Procedure

2-Hydroxybenzyl alcohol (15.0 g) and indene (75 g.) were heated at 210° for 1.5 hr. The unchanged indene was distilled off under reduced pressure and the residue chromatographed on silica gel, eluting with toluene. The product thus obtained, was recrystallised from cyclohexane to yield cis-4b,10,10a,11-tetrahydrobenz(b)indeno(2,1-e)pyran, 2.54 g., m.pt. 59°-60°. The product was characterised by its 1H-n.m.r spectrum. Isomeric purity was established by 13C-n.m.r spectroscopy

Workup

  1. distillationThe unchanged indene was distilled off under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washeluting with toluene
  4. customThe product thus obtained
  5. customwas recrystallised from cyclohexane

Sources & evidence

ORD record
ord-4cd27713aacf4622a168573b687150c5
Source dataset
uspto-grants-1984_06
Patent number
US04452991

Reaction notes

Loading…