Potassium Hydroxide → (2E)-3-{4-[(4-Hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoic acid

HRID 229168Notes

Reaction equation

HRID 229168 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:22]2[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][C:24]([CH3:31])([CH3:30])[CH2:23]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:22]2[CH2:23][C:24]([CH3:31])([CH3:30])[O:25][C:26]([CH3:29])([CH3:28])[CH2:27]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68978687Ethyl(2E)-3-{4-[(4-hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate

Product 1

HCID 11200188(2E)-3-{4-[(4-Hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Ethyl (2E)-3-{4-[(4-hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate (54) (0.1095 g, 0.260 mmole) was dissolved in ethanol (5 mL). Potassium hydroxide (0.260 mL of a 3 M aqueous solution, 0.780 mmole) was added and the mixture was heated to 75° C. for 2.5 h. The solution was cooled to RT and concentrated. Water (25 mL) was added and the mixture was extracted with ether (10 mL). The organics were thrown out and the aqueous layer was treated with 1 N aqueous HCl to pH=3. The resulting mixture was extracted with methylene chloride (3×10 mL). The organics were dried (Na2SO4) and concentrated to provide 0.097 g (95%) of compound 55 as a pale yellow solid. 1H NMR (DMSO-d6): δ 12.33 (s, 1H), 9.34 (s, 1H), 7.59 (d, J=8.2 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.15 (d, J=8.2 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 6.67 (d, J=8.4 Hz, 2H), 6.44 (d, J=15.9 Hz, 1H), 2.14 (s, 2H), 2.11(s, 2H), 1.11 (s, 6H), 1.10 (s, 6H). LRMS (ESI): m/z 391 (M−H)−.

Workup

  1. temperatureThe solution was cooled to RT
  2. concentrationconcentrated
  3. additionWater (25 mL) was added
  4. extractionthe mixture was extracted with ether (10 mL)
  5. additionthe aqueous layer was treated with 1 N aqueous HCl to pH=3
  6. extractionThe resulting mixture was extracted with methylene chloride (3×10 mL)
  7. dry with materialThe organics were dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fdcc31f9207246a091f8a6f0999ac98e
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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