Hydrochloric Acid → (2E)-3-{4-[(4-Hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoic acid

HRID 229139Notes

Reaction equation

HRID 229139 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])[CH2:25][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-].[Na+].Cl>C1COCC1.CCO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:22]2[CH2:23][C:24]([CH3:31])([CH3:30])[CH2:25][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:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68977877Ethyl(2E)-3-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoate

Product 1

HCID 11303858(2E)-3-{4-[(4-Hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoic acidYield 83,188.898%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of ethyl (2E)-3-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoate (15) (7.75 g, 0.0185 mmol) in THF (100 mL) and EtOH (100 mL) was slowly added 1 N NaOH (93 mL) solution at RT. The reaction mixture was heated to 70° C. and stirred at that temperature for 4.5 h. Reaction mixture was cooled to room temperature and then poured into 20% aqueous HCl (350 mL). The product was separated out as an off-white solid. The suspension was filtered and the filtered solid was dried to afford 6.01 g (83%) of compound 16 as an off-white solid. mp 219-220° C. 1H NMR (300 MHz, DMSO-d6): δ 0.89 (s, 6H), 0.90 (s, 6H), 1.27 (s, 2H), 1.91 (s, 2H), 1.94 (s, 2H), 6.47 (d, J=15.9 Hz, 1H), 6.68 (d, J=8.1 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 7.16 (d, J=8.1 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.60 (d, J=8.1 Hz, 2H), 9.31 (s, 1H), 12.35 (s, 1H). LRMS (ESI): m/z 389 (M−H)−.

Workup

  1. customat RT
  2. customReaction mixture
  3. temperaturewas cooled to room temperature
  4. customThe product was separated out as an off-white solid
  5. filtrationThe suspension was filtered
  6. customthe filtered solid was dried

Sources & evidence

ORD record
ord-8c4951eb75d04340813c41428a2ec899
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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