Potassium Hydroxide → 6-[3-(1-Adamantyl)-4-(3-hydroxypropyloxy)phenyl]-2-naphthoic acid

HRID 1078496Notes

Reaction equation

HRID 1078496 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[CH:28]=[C:27]([C:32]([O:34]C)=[O:33])[CH:26]=[CH:25]5)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[K+]>C(O)CCC>[C:1]12([C:11]3[CH:12]=[C:13]([C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[CH:28]=[C:27]([C:32]([OH:34])=[O:33])[CH:26]=[CH:25]5)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19429715HCID 19429715, compound

Product 1

HCID 102262546-[3-(1-Adamantyl)-4-(3-hydroxypropyloxy)phenyl]-2-naphthoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

0.57 g (1.21 mmol) of the ester obtained in Example 7 in suspension in 30 ml of n-butanol is treated with 400 mg of potassium hydroxide. The reaction mixture is heated for 3 h at 100° C., then evaporated to dryness, and is taken up in 50 ml of water and washed with ether. The aqueous phase is acidified to pH=1 with concentrated HCl and extracted with 600 ml of ether. The organic phase is washed with water, dried over magnesium sulphate, filtered and evaporated to give 0.49 g (90%) of the expected acid which melts at 277°-279° C.

Workup

  1. customevaporated to dryness
  2. washwashed with ether
  3. extractionextracted with 600 ml of ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-76be9a388bbb4341ae0d89b6472683ae
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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