Sodium Hydroxide → 2-Hydroxy-4-(3-phenoxypropoxy)benzoic acid

HRID 2163723Notes

Reaction equation

HRID 2163723 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22751303Methyl 2-hydroxy-4-(3-phenoxypropoxy)benzoate

Product 1

HCID 203314372-Hydroxy-4-(3-phenoxypropoxy)benzoic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-hydroxy-4-(3-phenoxypropoxy)benzoate (18.55g), methanol (40ml) and 10% aqueous sodium hydroxide (100ml) was stirred at 60° until a clear solution was obtained, then cooled and acidified. The precipitated solid was collected and recrystallised from cyclohexane-ethanol to give 15.09g (85%) of acid of mp 161°. (Found; C, 66.46; H, 5.71; C16H16O5 requires; C, 66.65; H, 5.59%).

Workup

  1. customwas obtained
  2. temperaturecooled
  3. customThe precipitated solid was collected
  4. customrecrystallised from cyclohexane-ethanol

Sources & evidence

ORD record
ord-7c22c7be0a534c9bb61b377025dc81ac
Source dataset
uspto-grants-1979_01
Patent number
US04136192

Reaction notes

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