Sodium Hydroxide → 4-(4-formylphenoxy)butanoic Acid

HRID 1360995Notes

Reaction equation

HRID 1360995 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=1)C.[OH-].[Na+]>CO>[CH:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:17])=[O:3])=[CH:10][CH:11]=1)=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15517709Ethyl 4-(4-formylphenoxy)butanoate

Product 1

HCID 35191904-(4-formylphenoxy)butanoic AcidYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Formylphenoxy)butyric acid ethyl ester (19.6 g, 75 mmol) was dissolved in methanol (250 mL) and 1N sodium hydroxide (100 mL) was added and the resulting mixture was stirred at room temperature for 16 hours. The organic solvent was evaporated in vacuo (40° C., 120 mBar) and the residue was acidified with 1N hydrochloric acid (110 mL). The mixture was filtered and washed with water and dried in vacuo to afford 14.3 g (91%) 4-(4-formylphenoxy)butyric acid as a solid. 1H-NMR (DMSO-d6): δ 1.99 (2H, p), 2.42 (2H, t), 4.13 (2H, t), 7.14 (2H, d), 7.88 (2H, d), 9.90 (1H, s), 12.2 (1H, bs). HPLC-MS (Method A): m/z=209 (M+1); Rt=2.19 min.

Workup

  1. customThe organic solvent was evaporated in vacuo (40° C., 120 mBar)
  2. filtrationThe mixture was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e4414adef0194a80a6bf8b5aeac05f7c
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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