Hydrochloric Acid → 2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethanone

HRID 1460227Notes

Reaction equation

HRID 1460227 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:14][CH2:15][C:16](Cl)=[O:17].Cl>C(=S)=S>[Cl:14][CH2:15][C:16]([C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[C:3]([O:2][CH3:1])[CH:8]=1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 460GuaiacolHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2421842-chloro-1-(4-hydroxy-3-methoxyphenyl)ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a cooled (ice bath) stirred solution of 130.3 g (1.05 mole) of 2-methoxyphenol in 750 mL of carbon disulfide was continuously added 306.6 g (2.3 mole) of anhydrous aluminum chloride portionwise. The stirred, cooled mixture was then treated dropwise with 80 mL (113 g, 1.0 mole) of 2-chloroacetyl chloride. After the addition was completed, the mixture was heated at reflux temperature for 20 hr, cooled, and poured into a mixture of 2 kg of crushed ice and 200 ml of concentrated hydrochloric acid. The solid which gradually crystallized was washed with water and carbon disulfide and dried. The solid was recrystallized from isopropyl ether containing a few drops of 2-propanol to yield 128.3 g (64% yield) of the title compound, mp 102°-103° C.

Workup

  1. temperatureTo a cooled (ice bath)
  2. temperatureThe stirred, cooled mixture
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux temperature for 20 hr
  6. temperaturecooled
  7. customThe solid which gradually crystallized
  8. washwas washed with water and carbon disulfide
  9. customdried
  10. customThe solid was recrystallized from isopropyl ether containing a few drops of 2-propanol

Sources & evidence

ORD record
ord-77705a8a434a4670a358ecae09b3fac4
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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