Hydrochloric Acid → 4-(10-Allyloxydecyloxy)benzoic acid

HRID 1612579Notes

Reaction equation

[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]I)[CH:2]=[CH2:3].C[O:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].Cl>C(O)C>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([OH:19])=[O:17])=[CH:21][CH:22]=1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

70 mmol (22.7 g) of 10-iododecyl allyl ether, 70 mmol (10.6 g) of methyl p-hydroxybenzoate, and 70 mmol (9.6 g) of potassium carbonate were refluxed in absolute ethanol for 15 hours. After addition of an aqueous potassium hydroxide solution (containing 4.0 g of potassium hydroxide) into the reaction solution, the resulting mixture was further heated at 80° C. for 5 hours. After conclusion of the reaction, the reaction solution was acidified with hydrochloric acid, and the acidified reaction solution was then concentrated under reduced pressure. Water was added to the residue to form a suspension, and the insoluble matter was collected and was then dried, to obtain 18.7 g of 4-(10-allyloxydecyloxy)benzoic acid. (Yield: 80%)

Workup

customAfter conclusion of the reaction
customthe acidified reaction solution
concentrationwas then concentrated under reduced pressure
additionWater was added to the residue
customto form a suspension
customthe insoluble matter was collected
customwas then dried

Sources & evidence

ORD record: ord-84dc5b0f78bb4e8d9ed2b74d4b43b006
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190687

Reaction notes

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