Hydrochloric Acid → Benzyl 2,4-dihydroxyphenyl ketone

HRID 437266Notes

Reaction equation

HRID 437266 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH2:9]([C:16]#N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.CC[O:21][CH2:22][CH3:23]>[Cl-].[Zn+2].[Cl-]>[CH2:9]([C:22]([CH2:23][C:1]1[CH:8]=[CH:7][CH:6]=[CH:4][CH:3]=1)=[O:21])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1.[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[OH:21].[CH2:9]([C:16]([C:6]1[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=1[OH:5])=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5054ResorcinolHCID 8794Phenylacetonitrile

Product 2

HCID 138005Benzyl 2,4-dihydroxyphenyl ketoneHCID 21430150HCID 21430150, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

The 2,4-dihydroxyphenol benzyl ketone was prepared by treating a mixture of 100 parts of resorcinol, 100 parts of benzyl cyanide and 20 parts of anhydrous zinc chloride in dry ether with hydrogen chloride gas saturated. After standing for 2 days the lower oily layer was separated off, washed with ether by decantation and boiled with 200 parts of water for 2 hours. After cooling the yellow crystals were collected by filtrate and dried. Crystallisation from benzene gave 2,4-dihydroxyphenyl benzyl ketone as yellow/orange crystals, melting at 113°-114° C.

Workup

  1. additionby treating
  2. customthe lower oily layer was separated off
  3. washwashed with ether by decantation
  4. waitboiled with 200 parts of water for 2 hours
  5. temperatureAfter cooling the yellow crystals
  6. customwere collected by filtrate
  7. customdried
  8. customCrystallisation from benzene

Sources & evidence

ORD record
ord-74dde539ee1840239afbfe09e0528b46
Source dataset
uspto-grants-1977_06
Patent number
US04029704

Reaction notes

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