Sodium Carbonate → 9-Hydroxy-7-(3-methyl-2-octyl)-2,2,-dimethyl-4-oxo-1,2,3,4-tetrahydrocyclopenta[c] [1]benzopyran

HRID 267342

Reaction equation

HRID 267342 reaction equation
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].[CH3:18][C:19]1([CH3:30])[CH2:23][C:22](=O)[CH:21]([C:25](OCC)=[O:26])[CH2:20]1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[OH:10][C:9]1[C:8]2[C:22]3[CH2:23][C:19]([CH3:30])([CH3:18])[CH2:20][C:21]=3[C:25](=[O:26])[O:12][C:7]=2[CH:6]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 11735559Ethyl 4,4-dimethyl-2-oxocyclopentane-1-carboxylate

Product 1

HCID 541338539-Hydroxy-7-(3-methyl-2-octyl)-2,2,-dimethyl-4-oxo-1,2,3,4-tetrahydrocyclopenta[c] [1]benzopyran

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

to 13.5 g. of 5-(3-methyl-2-octyl)-resorcinol and 10.5 g. of 4,4-dimethyl-2-carboethoxycyclopentanone [Canadian J. of Chem. 47, 1982-1988 (1969)] in 59 ml. of benzene was added 4.3 ml. of phosphorus oxychloride with stirring and refluxing for 6 hours. The red solution was let stand at room temperature for 8 hours, poured into ice and sodium carbonate solution. The colorless mixture was extracted with ether, dried over magnesium sulfate and concentrated. The mixture was extracted with cold pentane and the pentane was discarded. The residue [9-hydroxy-7-(3-methyl-2-octyl)-2,2-dimethyl-4-oxo-1,2,3,4-tetrahydrocyclopenta[ c][1]benzopyran] was obtained as a gummy solid.

Workup

  1. temperaturerefluxing for 6 hours
  2. customat room temperature
  3. customfor 8 hours
  4. extractionThe colorless mixture was extracted with ether
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. extractionThe mixture was extracted with cold pentane

Sources & evidence

ORD record
ord-11315d3d7c174797a95fe7c427770b3b
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Linked notes

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