Methanol → 4-(9-Decen-1-yloxy)benzoic acid

HRID 2050419Notes

Reaction equation

HRID 2050419 reaction equation
[CH2:1]([O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[OH-].[K+].O.CO>C(OCC)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 19834780Methyl 4-(9-decenyloxy)benzoate

Product 1

HCID 148765254-(9-Decen-1-yloxy)benzoic acidYield 43.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 17 g of methyl 4-(9-decenyloxy)benzoate. 17 g of potassium hydroxide, 20 ml of water and 200 ml of methanol was heated to 75° C. on an oil bath for 4 hours. The cooled mixture was treated with 100 ml of ice-cold 3N hydrochloric acid and the liberated acid was taken up in 150 ml of diethyl ether. The separated aqueous phase was back-extracted twice with 100 ml of diethyl ether each time. The combined organic phases were washed with 50 ml of 2N sodium carbonate solution and several times with water, dried over magnesium sulphate and concentrated. Recrystallization of the crude product obtained from ethanol gave 7 g of 4-(9-decenyloxy)benzoic acid, m.p. (C-SC) 77° C., phase transition (SC -N) 116° C., cl.p. (N-I) 137° C.

Workup

  1. extractionThe separated aqueous phase was back-extracted twice with 100 ml of diethyl ether each time
  2. washThe combined organic phases were washed with 50 ml of 2N sodium carbonate solution and several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customRecrystallization of the crude product
  6. customobtained from ethanol

Sources & evidence

ORD record
ord-59e252039b744d25b349cc9dd19dcd2f
Source dataset
uspto-grants-1991_05
Patent number
US05013476

Reaction notes

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