Hydrochloric Acid → HCID 12906128, compound

HRID 647034Notes

Reaction equation

HRID 647034 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:17].Cl>ClCC(Cl)(Cl)Cl.O>[OH:10][C:3]1[C:2]([CH3:1])=[C:7]([CH3:8])[CH:6]=[C:5]([CH3:9])[C:4]=1[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 127692,3,5-Trimethylphenol2×HCID 14065Hexanoic acid, 6-chloro-6-oxo-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12906128HCID 12906128, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

To a solution of 2,3,5-trimethylphenol(formula VII wherein R=H3C, X=H, Y=OH) (1.4 part) in tetrachloroethane (10 volume parts), there was added a solution of aluminum chloride dust (3.5 parts) and ethyl 5-chloroformylpentanoate (3 parts) in tetrachloroethane (5 volume parts) at 0° C. and in a current of nitrogen gas and the mixture was heated at 110°-120° C. for 17 hours. To the reaction mixture was added cold water (50 volume parts) and the dilution was acidified with dilute hydrochloric acid and extracted with chloroform (200 volume parts). The residue (2.7 parts) obtained from the extract was subjected to column chromatography on silicic acid (60 parts) and eluted with chloroform-diethyl ether (20:1) (300 volume parts). The eluate was evaporated to dryness and the residue was recrystallized from ethanol. The procedure provided colorless needles of ethyl 5-(2'-hydroxyl-3',4',6'-trimethylbenzoyl)pentanoate (formula II-1 wherein R=H3C, X=H, Y=OH, n=4, in the form of ethyl ester) (1.9 part) melting at 72°-73° C.

Workup

  1. temperaturein a current of nitrogen gas and the mixture was heated at 110°-120° C. for 17 hours
  2. extractionextracted with chloroform (200 volume parts)
  3. customThe residue (2.7 parts) obtained from the extract
  4. washeluted with chloroform-diethyl ether (20:1) (300 volume parts)
  5. customThe eluate was evaporated to dryness
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-12e1d27fb51f4243bfa64c62b77a76a3
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

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