Sodium Hydroxide → 2-Benzyloxy-4-phenylethynylbenzoic acid

HRID 322863Notes

Reaction equation

HRID 322863 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([C:25]#[C:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([C:25]#[C:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10598112Benzyl 2-benzyloxy-4-phenylethynyl-benzoate

Product 1

HCID 107586542-Benzyloxy-4-phenylethynylbenzoic acidYield 38.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of benzyl 2-benzyloxy-4-phenylethynylbenzoate (2 g) and 1 N sodium hydroxide (5 mL) in dioxan (80 mL) is heated at reflux for 1 hour. The reaction mixture is evaporated, the residue dissolved in water (6 mL) and the solution washed twice with ethyl acetate (20 mL). The pH of the aqueous phase is adjusted to pH 1 by addition of 2 N hydrochloric acid and resulting solid is filtered and washed well with water to give 2-benzyloxy-4-phenylethynylbenzoic acid (0.6 g), m.p. 125-127° C. [Elemental analysis:- C,80.2; H,4.86%. Calculated:- C,80.5; H,4.91%].

Workup

  1. temperatureat reflux for 1 hour
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue dissolved in water (6 mL)
  4. washthe solution washed twice with ethyl acetate (20 mL)
  5. additionThe pH of the aqueous phase is adjusted to pH 1 by addition of 2 N hydrochloric acid
  6. customresulting solid
  7. filtrationis filtered
  8. washwashed well with water

Sources & evidence

ORD record
ord-b13fe510386d4abead8d32256efd355e
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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