Sodium Hydroxide → HCID 54129165, compound

HRID 355800Notes

Reaction equation

HRID 355800 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>C1COCC1.CO>[OH:1][C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675533HCID 22675533, compound

Product 1

HCID 54129165HCID 54129165, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-hydroxy-4-[2-(phenethyl)phenethyl]benzoate (0.25 g) in THF (5 ml) and methanol (5 ml) containing aqueous 2N sodium hydroxide (5 ml) was heated under reflux for 2 hours. The reaction mixture was evaporated to small volume and acidified with aqueous 2N hydrochloric acid. The mixture was extracted three times with ethyl acetate (25 ml each time) and the combined extracts were washed with brine and dried over anhydrous magnesium sulphate. The solid obtained on removal of the solvent was crystallised from a mixture of diethyl ether and hexane to give 2-hydroxy-4-[(2-phenethyl)phenethyl]benzoic acid (0.2 g), m.p. 134°-7° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe reaction mixture was evaporated to small volume
  4. extractionThe mixture was extracted three times with ethyl acetate (25 ml each time)
  5. washthe combined extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe solid obtained on removal of the solvent
  8. customwas crystallised from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-d5d80f3331584ec49027d20defb6a85b
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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