Hydrochloric Acid → 4-METHYLPHENYL 4-CHLOROBUTANOATE

HRID 325746Notes

Reaction equation

HRID 325746 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].Cl>C1(C)C(C)=CC=CC=1>[Cl:9][CH2:10][CH2:11][CH2:12][C:13]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2879P-CresolHCID 783704-Chlorobutyryl chloride

Product 1

HCID 48490374-METHYLPHENYL 4-CHLOROBUTANOATEYield 95.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-methylphenol (54 g) and 4-chlorobutyryl chloride (77.5 g) was dissolved in xylene (250 ml). The mixture was heated gently until, at about 130° C., a vigorous reaction occurred. After the reaction had subsided, the mixture was heated at reflux for approximately 40 minutes, until the evolution of hydrogen chloride had ceased. The xylene was then removed in vacuo, and the residue was distilled to give 4-methylphenyl 4-chlorobutyrate (101 g), b.p. 116°-118° C./0.2 mm Hg.

Workup

  1. customa vigorous reaction
  2. temperaturethe mixture was heated
  3. customThe xylene was then removed in vacuo
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-399448bb52c941dd811ebda77ed8a6e3
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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