Hexanoyl chloride → HCID 86742841, compound

HRID 1194827Notes

Reaction equation

HRID 1194827 reaction equation
C(Cl)(=O)CCCCC.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:13][CH:14]([CH2:25][CH2:26][CH3:27])[CH:15]([OH:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.Cl.[NH2:29][OH:30]>C(O)C.N1C=CC=CC=1.CCCCCCC.C(O)C.O>[Cl:13][CH:14]([CH2:25][CH2:26][CH3:27])[CH:15]([OH:24])[C:16](=[N:29][OH:30])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 67340Hexanoyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 6451240Aluminum(III) ChlorideHCID 21268919HCID 21268919, compound

Product 1

HCID 86742841HCID 86742841, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 8900HeptaneSolventHCID 19096565Water ethanolSolvent

Procedure

o-chloropheol and caproylchloride are converted in a wellknown mode to ester which with aluminium chloride, according to Fries, is rearranged by one-hour heating to 120° C. to 3-chloro-2-hydroxy-caprophenone, between 78° C. and 80° C. in flash point (ethanol/water, n-heptane). 22.6 g (0.1 Mol) of ketone are boiled three hours, along with reflux cooling, together with 15.2 (0.22 Mol) of hydroxylamine hydrochloride in 150 ml of absolute ethanol and 25 ml of pyridine. An oily residue is left, following evaporation of the solvent under vacuum conditions. The oxime, 102° C. to 103° C. in flash point, is obtained from treatment with ethanol/water and recrystallisation from n-heptane.

Workup

  1. waitis rearranged by one-hour
  2. temperaturealong with reflux
  3. waitAn oily residue is left
  4. customevaporation of the solvent under vacuum conditions

Sources & evidence

ORD record
ord-c5b79139453d4281a70e86ea9688f326
Source dataset
uspto-grants-1989_03
Patent number
US04816487

Reaction notes

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