Chloroform → 4-Vinylbenzoyl chloride

HRID 1755499Notes

Reaction equation

HRID 1755499 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].C(C1C=C(O)C(=CC=1)O)(C)(C)C.C(Cl)(Cl)[Cl:25].C(Cl)(=O)C(Cl)=O>CN(C)C=O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:25])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 73814-tert-ButylcatecholHCID 140984-Vinylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 110520284-Vinylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a reaction vessel fitted with a cooling pipe, a stirrer, a thermometer and a nitrogen feed pipe, 20 parts of formula-(21) 4-vinylbenzoic acid, 0.6 part of 4-tert-butylcatechol and 225 parts of chloroform were fed, and then cooled to 15° C. or below. While keeping the liquid temperature at 15° C. or below, 2.8 parts of dehydrated N,N-dimethylformamide was added, and then 87.4 parts of oxalyl chloride was dropwise added thereto. After its addition made dropwise, the liquid temperature was raised to room temperature, followed by stirring for 20 hours. After the reaction was completed, the solvent was evaporated off under reduced pressure, and then 340 parts of n-heptane was added. The organic layer formed was washed with ion-exchanged water, and this organic layer was dried with magnesium sulfuric anhydride, followed by evaporation of the solvent under reduced pressure to obtain a crude product of formula-(22) 4-vinylbenzoic acid chloride (21.8 parts).

Workup

  1. customInto a reaction vessel fitted with a cooling pipe, a stirrer
  2. temperaturecooled to 15° C. or below
  3. customat 15° C. or below
  4. additionAfter its addition
  5. customthe solvent was evaporated off under reduced pressure
  6. addition340 parts of n-heptane was added
  7. customThe organic layer formed
  8. washwas washed with ion-exchanged water
  9. dry with materialthis organic layer was dried with magnesium sulfuric anhydride
  10. customfollowed by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1d60a81c78244e8fb4c1652a9a3a3be2
Source dataset
uspto-grants-2015_10
Patent number
US09170514B2

Reaction notes

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