Sodium Hydroxide → 4-(1-Hydroxy-2-methylpropan-2-yl)-3-methoxybenzoic acid

HRID 1405406Notes

Reaction equation

HRID 1405406 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[CH:21]=[CH:20][C:9]([C:10]([O:12]CC2C=CC=CC=2)=[O:11])=[CH:8][C:7]=1[O:22][CH3:23])([CH3:5])[CH3:4].[OH-].[Na+]>C1COCC1>[OH:1][CH2:2][C:3]([C:6]1[CH:21]=[CH:20][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:22][CH3:23])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68153567Benzyl 4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxybenzoate

Product 1

HCID 681532344-(1-Hydroxy-2-methylpropan-2-yl)-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the crude benzyl 4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxybenzoate (from step 3) was added THF (2 mL) followed by aqueous NaOH (1.7 mL of 3.0 M, 5.0 mmol). The reaction mixture was stirred for 3 h. The reaction mixture was acidified to pH 3 and was extracted with EtOAc 3 times. The organic layers were dried over sodium sulfate and the solvent was evaporated to give 4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxybenzoic acid. ESI-MS m/z calc. 224.1, found 224.2 (M+1)+; Retention time: 2.46 minutes (4 min run).

Workup

  1. extractionwas extracted with EtOAc 3 times
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-735f870968a24bc7b1b3de6f32f2fe86
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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