1-Butanol → HCID 86735530, compound

HRID 971641Notes

Reaction equation

HRID 971641 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])C)=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13]([OH:17])[CH2:14]CC.BrBr.CC1C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1.C(O)CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:10][CH2:14][CH2:13][O:17]2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 24408BromineHCID 194294681-(4-Chloro-2-methoxyphenyl)ethan-1-one

Product 1

HCID 86735530HCID 86735530, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 27.5 parts of 1-(4-chloro-2-methoxyphenyl)ethanone in 160 parts of butanol are added dropwise 24 parts of bromine. After stirring for 1 hour at room temperature, there are added successively 9.3 parts of 1,2-ethanediol, 3 parts of 4-methylbenzenesulfonic acid and 450 parts of benzene. Stirring is continued overnight at reflux temperature with water-separator. The reaction mixture is evaporated and the residue is taken up in benzene. The mixture is washed with a diluted sodium hydroxide solution and three times with water, dried, filtered and evaporated. The residue is crystallized from methanol, yielding 27.6 parts (60%) of 2-(bromomethyl)-2-(4-chloro-2-methoxyphenyl-1,3-dioxolane; mp. 110° C.

Workup

  1. stirringStirring
  2. waitis continued overnight
  3. customThe reaction mixture is evaporated
  4. washThe mixture is washed with a diluted sodium hydroxide solution and three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-268a30ce79ab46ae9f54046d90e16ea1
Source dataset
uspto-grants-1979_07
Patent number
US04160838

Reaction notes

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