Hydrogen iodide → Orcinol

HRID 1609402

Reaction equation

HRID 1609402 reaction equation
I.C[O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11]C)[CH:5]=1>>[CH3:10][C:8]1[CH:7]=[C:6]([OH:11])[CH:5]=[C:4]([CH:9]=1)[OH:3]

Participants

3

Reactant 2

HCID 24841Hydrogen iodideHCID 778443,5-Dimethoxytoluene

Product 1

HCID 10436Orcinol

Procedure

Methylmagnesium bromide (35 g) was added to 1,3-dimethoxy-5-benzoyl chloride (100 g) to obtain 1,3-dimethoxy-methylphenone in a yield of 45%. Then, the reduction was conducted by adding water (300 cc), concentrated hydrochloric acid (300 cc) and 1,3-dimethoxy-methylphenone (100 g) to zinc amalgam obtained from zinc (400 g) and mercuric chloride (20 g). Further, concentrated hydrochloric acid (10 to 15 cc) was added every one hour. After the completion of the reaction, the reaction solution was cooled and saturated with sodium chloride, and then extracted with ether to obtain 40 g of 1,3-dimethoxy-5-methylbenzene. Hydrogen iodide was added to the resulting 1,3-dimethoxy-5-methylbenzene and stirred at 115° to 125° C. for 3 hours under nitrogen atmosphere. After cooling, the product was extracted with methylene chloride to obtain 30 g of 5-methylresorcinol.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with methylene chloride

Sources & evidence

ORD record
ord-95315044872d4612af294f918464c28a
Source dataset
uspto-grants-1995_03
Patent number
US05399785

Linked notes

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