Hydrochloric Acid → 1-(2,4-Dihydroxy-5-isopropylphenyl)ethanone

HRID 2425022Notes

Reaction equation

HRID 2425022 reaction equation
Cl.[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12])([CH3:4])[CH3:3].[CH3:13][C:14]#N.[OH2:16]>CCOCC.[Cl-].[Cl-].[Zn+2]>[OH:11][C:8]1[CH:7]=[C:6]([OH:12])[C:5]([CH:2]([CH3:4])[CH3:3])=[CH:10][C:9]=1[C:14](=[O:16])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6342AcetonitrileHCID 901354-Isopropylresorcinol

Product 1

HCID 247733601-(2,4-Dihydroxy-5-isopropylphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Dry HCl was passed through a suspension of 4-isopropyl-1,3-benzenediol (17.01 g; 112 mmol), CH3CN (8.3 ml; 158 mmol) and fused ZnCl2 (14 g) in dry ether (100 ml) for 1 h at 0° C. The reaction mixture was then stirred for 1 h at room temperature and filtered. The solid obtained was hydrolyzed with boiling water as reported in the literature. The crude product was purified using flash chromatography (silica gel, 3% CH3CN in chloroform). Yield, 15.2 g (69.6%); mp, 142-44° C.; MS (CI): 223 (M++29), 195 (M++1), 179; analysis: C11H14O3 requires: C, 68.02; H, 7.26; found C, 68.40; H, 7.33%.

Workup

  1. filtrationfiltered
  2. customThe solid obtained
  3. customThe crude product was purified
  4. customYield
  5. custommp, 142-44° C.

Sources & evidence

ORD record
ord-dbae39f4c36942208423153f31613780
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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