Hydrochloric Acid → 4-Undecylphenylacetic acid

HRID 1650813Notes

Reaction equation

HRID 1650813 reaction equation
[CH2:1]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=[O:20])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH-].[Na+].Cl>CO.O1CCCC1>[CH2:1]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23052528Ethyl 4-undecylphenylacetate

Product 1

HCID 230525324-Undecylphenylacetic acidYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of ethyl 4-undecylphenylacetate (7.2 g, 0.023 mol) in a mixture of methanol (40 ml) and tetrahydrofuran (40 ml) was added sodium hydroxide (2.2 g, 0.055 mol) and stirred at 50° C. for 20 minutes. The reaction mixture was adjusted to pH 4 with 2N hydrochloric acid after concentration. The resultant mixture was extracted with ethyl acetate, and the organic layer was washed with water, dried and concentrated under reduced pressure. The resulting crude crystals were recrystallized from hexane to obtain 4-undecylphenylacetic acid (3-x, 1.8 g, 27%). m.p. 83°-84° C.

Workup

  1. concentrationafter concentration
  2. extractionThe resultant mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-b2b03930f87047c69da2b928da8f1e0b
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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