4-(3-Chloropropoxy)-3-methoxyacetophenone → 1-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanone

HRID 2379939Notes

Reaction equation

HRID 2379939 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[O:15]C>OS(O)(=O)=O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[OH:15]

Participants

3

Reactant 1

HCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenone

Product 1

HCID 103765071-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanoneYield 36.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (10.0 g, 0.0412 mol) and concentrated H2SO4 (50 ml) was stirred at 65° for 23 hours. The cooled reaction was poured into 250 g of ice and was stirred vigorously for 10 minutes. The aqueous mixture was extracted with dichloromethane (CH2Cl2) and the resultant dichloromethane extract was washed well with 5% sodium hydroxide. The basic phases were combined and washed with dichloromethane. The aqueous mixture was cooled in an ice bath and concentrated hydrochloric acid was added until a precipitate formed. The product was isolated by filtration and dried to yield 3.1 of a light brown solid. This was combined with an additional sample (5.0 g total) and two consecutive recrystallizations from toluene provided 3.4 g (22%) of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone as a beige solid, m.p.=101°-103° C.

Workup

  1. customThe cooled reaction
  2. stirringwas stirred vigorously for 10 minutes
  3. extractionThe aqueous mixture was extracted with dichloromethane (CH2Cl2)
  4. extractionthe resultant dichloromethane extract
  5. washwas washed well with 5% sodium hydroxide
  6. washwashed with dichloromethane
  7. temperatureThe aqueous mixture was cooled in an ice bath
  8. additionconcentrated hydrochloric acid was added until a precipitate
  9. customformed
  10. customThe product was isolated by filtration
  11. customdried
  12. customto yield 3.1 of a light brown solid
  13. customThis was combined with an additional sample (5.0 g total) and two consecutive recrystallizations from toluene

Sources & evidence

ORD record
ord-003f40977b6a4708bd2d5c1216d7c9ae
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

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