Hydrochloric Acid → HCID 20282962, compound

HRID 463342Notes

Reaction equation

HRID 463342 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[CH2:6][CH3:7].[C:16]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17]1.ClCC(Cl)(Cl)Cl.Cl>[N+](C1C=CC=CC=1)([O-])=O>[O:23]=[C:16]([C:12]1[CH:11]=[CH:10][C:9]([O:14][CH3:15])=[C:8]([CH2:5][CH2:6][CH3:7])[CH:13]=1)[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7940Glutaric anhydrideHCID 124181,1,1,2-TetrachloroethaneHCID 6451240Aluminum(III) ChlorideHCID 125237921-Methoxy-2-propylbenzene

Product 1

HCID 20282962HCID 20282962, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Aluminium chloride (112 g) was slowly added over one hour to a stirred mixture of o-propylanisole (60 g), glutaric anhydride (50.5 g), tetrachloroethane (880 ml) and nitrobenzene (200 ml) maintained between 3°-4°. The mixture was stirred for two days and then poured into dilute hydrochloric acid. The organic phase was steam distilled, and the residue remaining was extracted with ether, which was then extracted with sodium bicarbonate solution. Acidification and crystallisation from ethylacetate-light petroleum (bp 60°-80°) gave 5-oxo-5-(4-methoxy-3-propylphenyl)pentanoic acid (70 g), mp 105°-106°. This acid was refluxed with zinc amalgam (270 g), dioxan (300 ml), toluene (300 ml), and concentrated hydrochloric acid (100 ml) for two days. Extraction with ether and subsequent evaporation gave an oil, which crystallised from cyclohexane to give 5-(4-methoxy-3-propylphenyl)pentanoic acid (36 g), mp 84°. This acid was esterified with methanol and concentrated sulphuric acid, and the methyl ester so obtained (26 g) was added to a stirred suspension of lithium aluminium hydride (3 g) in tetrahydrofuran at 0°. The mixture was refluxed for 3 hours, cooled, treated with water, and extracted with ether, which on evaporation gave the title alcohol (16 g), mp 34.5°-35°.

Workup

  1. temperaturemaintained between 3°-4°
  2. distillationdistilled
  3. extractionthe residue remaining was extracted with ether, which
  4. extractionwas then extracted with sodium bicarbonate solution
  5. customAcidification and crystallisation from ethylacetate-light petroleum (bp 60°-80°)

Sources & evidence

ORD record
ord-88486c6ec1374537a8c2a854d39ca637
Source dataset
uspto-grants-1985_05
Patent number
US04518612

Reaction notes

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