Sodium Hydroxide → HCID 18951537, compound

HRID 1492851Notes

Reaction equation

HRID 1492851 reaction equation
C[O:2][C:3](=[O:48])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH:7]=[C:6]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:36][CH:35]=2)[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:42]1([CH2:41][O:40][C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:32][CH2:31][CH2:30][O:29][C:6]3[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]4[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:19][CH:20]=4)[CH:7]=3)[C:3]([OH:48])=[O:2])=[CH:35][CH:36]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54529309HCID 54529309, compound

Product 1

HCID 18951537HCID 18951537, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.5 g (2.3 mmol) of 3,5-bis[3-[4-(phenylmethoxy) phenoxy]propoxy]benzoic acid methyl ester (prepared in Example 46) and 1.2 ml (7.2 mmol) of 6N NaOH in 25 ml of methanol and 10 ml of dioxane was stirred at reflux under argon for 19 hours. The solvents were removed at reduced pressure, the residue was acidified and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from acetone-hexane to give 1.37 g (93% yield, mp 139°-140°) of 3,5-bis[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid.

Workup

  1. temperatureat reflux under argon for 19 hours
  2. customThe solvents were removed at reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated to a solid which
  6. customwas recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-ae82feea55c448bcb039b0d511141c26
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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