Hydrochloric Acid → 3-(1-Adamantyl)-4-methoxybenzoic acid

HRID 710363Notes

Reaction equation

HRID 710363 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)[CH:5]=1.[OH-].[Na+].CCO.Cl>C1COCC1.O.CCOC(C)=O>[C:12]12([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=3[O:10][CH3:11])[C:3]([OH:22])=[O:2])[CH2:13][CH:14]3[CH2:20][CH:18]([CH2:17][CH:16]([CH2:15]3)[CH2:21]1)[CH2:19]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 14549070Methyl 3-(1-adamantyl)-4-methoxybenzoate

Product 1

HCID 52965033-(1-Adamantyl)-4-methoxybenzoic acidYield 90.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl-3-(1-adamantyl)-4-methoxybenzoate (0.27 g, 0.85 mmol) in THF (30 ml) was added a solution of NaOH (0.04 g) in H2O (1 ml), followed by the addition of EtOH (2 ml). The mixture was refluxed for 4 h, then cooled to room temperature and acidified with 1M HCl solution. The crude product was taken in EtOAc (100 ml) and the organic layer was washed with H2O, and dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title product (0.22 g, 85%) as colourless solid. 1H-NMR (CDCl3) 1.77 (s, 6H), 2.03 (s, 3H), 2.09 (s, 6H), 3.89 (s, 3H), 6.88 (d, 1H, J=8.44 Hz), 7.93-7.98 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. washthe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-fac5522abc9d48c5ac8fac7b3344b96f
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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