Tetrahydrofuran → 4-[(4,4-Dimethyl-cyclohexylidene)-(4-hydroxy-phenyl)-methyl]-benzoic acid

HRID 229247Notes

Reaction equation

HRID 229247 reaction equation
C1COCC1.C[O:7][C:8](=[O:31])[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[C:23]2[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH2:24]2)[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)C>[CH3:29][C:26]1([CH3:30])[CH2:25][CH2:24][C:23](=[C:15]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[C:12]2[CH:13]=[CH:14][C:9]([C:8]([OH:31])=[O:7])=[CH:10][CH:11]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 686544214-[(4,4-Dimethylcyclohexylidene)-(4-hydroxy-phenyl)-methyl]-benzoic acid methyl ester

Product 1

HCID 111518544-[(4,4-Dimethyl-cyclohexylidene)-(4-hydroxy-phenyl)-methyl]-benzoic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of THF (2 mL) and ethanol (2 mL) containing 4-[(4,4-dimethyl-cyclohexylidene)-(4-hydroxy-phenyl)-methyl]-benzoic acid methyl ester (171) (0.16 g, 0.457 mmol) was added 1 N NaOH (4 mL). The reaction mixture was heated at 65° C. for 4 h. The reaction mixture was partially concentrated to remove the EtOH and THF. To the basic aqueous mixture was added 1 N HCl to pH ˜1 (according to litmus paper). The acidic aqueous solution was extracted with dichloromethane and the organic extract was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was triturated with dichloromethane, filtered, and dried to give 0.132 g (85%) of the title compound 172 as a white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.93 (s, 6H), 1.32 (s, 4H), 2.12-2.19 (m, 4H), 6.66 (d, J=8.3 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 7.14 (d, J=8.1 Hz, 2H), 7.83 (d, J=8 Hz, 2H), 9.33 (s, 1H), 12.74 (s, 1H). HRMS (ESI) Calcd for C22H23O3: 335.1647 (M−H)−. Found: 335.1640.

Workup

  1. concentrationThe reaction mixture was partially concentrated
  2. customto remove the EtOH and THF
  3. additionTo the basic aqueous mixture was added 1 N HCl to pH ˜1 (according to litmus paper)
  4. extractionThe acidic aqueous solution was extracted with dichloromethane
  5. extractionthe organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was triturated with dichloromethane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-e6ba1b680c364e3fbb5f83309201bc58
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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