Allyl Alcohol → Allyl 2-chlorobenzoate

HRID 1249589Notes

Reaction equation

HRID 1249589 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([O:4][CH2:1][CH:2]=[CH2:3])=[O:16]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 348480Allyl 2-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sixty parts of allyl alcohol were dissolved in 240 parts of chloroform, followed by an addition of 105 parts of triethylamine. While stirring the resultant mixture at 10°-15° C., 175 parts of o-chlorobenzoyl chloride were added dropwise over 2 hours. After the resultant mixture was heated at 45°-50° C. for 3 hours, the liquid reaction mixture was poured in a separation funnel and washed first with dilute hydrochloric acid and then with water. The thus-formed light-yellowish organic layer was dried with calcium chloride and then treated with activated carbon. After driving chloroform off, the residue was distilled under reduced pressures to obtain 153 parts of allyl o-chlorobenzoate (hereinafter called "Compound A"; b.p. 101° C./3.5 mmHg).

Workup

  1. customthe liquid reaction mixture
  2. additionwas poured in a separation funnel
  3. washwashed first with dilute hydrochloric acid
  4. dry with materialThe thus-formed light-yellowish organic layer was dried with calcium chloride
  5. additiontreated with activated carbon
  6. distillationwas distilled under reduced pressures

Sources & evidence

ORD record
ord-81a57e085f734fdd84ee2817ce9e0fe4
Source dataset
uspto-grants-1986_12
Patent number
US04632969

Reaction notes

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