Sodium Hydroxide → (Rac)-alpha-methyl-6-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid

HRID 2108267Notes

Reaction equation

HRID 2108267 reaction equation
C[O:2][C:3](=[O:45])[CH:4]([CH3:44])[C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:23]=3[O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:11]=2)[CH:6]=1.[OH-].[Na+]>CO>[CH3:44][CH:4]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:23]=3[O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:11]=2)[CH:6]=1)[C:3]([OH:45])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15086660Rac.-alpha-methyl-6-[6[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid methyl ester

Product 1

HCID 15086663(Rac)-alpha-methyl-6-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.35 g (5.56 mmol) of rac.-alpha-methyl-6-[6[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid methyl ester in 100 mL of methanol and 3.7 mL (22 mmol) of 6N sodium hydroxide was stirred at reflux for 4 hours. The solvent was removed at reduced pressure, the residue was acidified and the product was filtered to give (rac)-alpha-methyl-6-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid. An analytical sample was obtained from ether-hexane.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe solvent was removed at reduced pressure
  3. filtrationthe product was filtered

Sources & evidence

ORD record
ord-7bc60953a223466fa296cb4e560476b4
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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