Hydrochloric Acid → 4-{10-(1,8-Nonadien-5-yloxy)decyloxy}benzoic acid

HRID 1755613Notes

Reaction equation

HRID 1755613 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH:8]=[CH2:9].[OH-].[K+].Cl>O.CO>[CH2:9]=[CH:8][CH2:7][CH2:6][CH:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=1)[CH2:4][CH2:3][CH:2]=[CH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19917652Methyl 4-{10-(1,8-nonadien-5-yloxy)decyloxy}benzoate

Product 1

HCID 199176464-{10-(1,8-Nonadien-5-yloxy)decyloxy}benzoic acidYield 94.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2.3 g of the compound (8) and 1.1 g of potassium hydroxide were dissolved in a solution mixture of 14 ml of water and 6 ml of methanol, and reflux was then carried out for 5 hours. The reaction solution was added into 100 ml of water, and the pH was adjusted approximately to 1 with concentrated hydrochloric acid. The waxen matter generated therein was washed with water and was then dried at 40° C. under reduced pressure, to obtain 2.1 g of the compound (9). (Yield: 93%)

Workup

  1. temperaturereflux
  2. washThe waxen matter generated therein was washed with water
  3. customwas then dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-f03389ed51074649a251e30fe3299ced
Source dataset
uspto-grants-1995_08
Patent number
US05437816

Reaction notes

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