Potassium Hydroxide → 4-Hydroxy-4-[3,4-dimethoxy-2-(1-methylethyl)phenyl]-3-methylbut-2-enoic Acid

HRID 1585265Notes

Reaction equation

HRID 1585265 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=1[CH:21]([CH3:23])[CH3:22])[C:3]([CH3:10])=[CH:4][C:5]([O:7]CC)=[O:6].[OH-].[K+]>C(O)C>[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=1[CH:21]([CH3:23])[CH3:22])[C:3]([CH3:10])=[CH:4][C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67591228Ethyl 4-Hydroxy-4-[3,4-dimethoxy-2-(1-methylethyl)phenyl]-3-methylbut-2-enoate

Product 1

HCID 675919944-Hydroxy-4-[3,4-dimethoxy-2-(1-methylethyl)phenyl]-3-methylbut-2-enoic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 8 (9.00 g, 27.9 mmol) was dissolved in 100 mL of ethanol with 3 g of KOH and refluxed for 1 h. The mixture was poured onto 100 g of ice with 25 ml of 6 M HCL and stirred for 24 h. The white solid was filtered, washed with water, dried and recrystallized from ether/petroleum ether to give 7.38 g (25.1 mmol, 90%) of 9 as white plates: mp 154-155° C.; IR 3411 (OH), 1694 (carbonyl), 1644 (alkene) cm-1 ; 1H NMR δ1.38 (d, J=7.0 Hz, 6H), 2.00 (s, 3H), 3.44 (br s, 1H), 3.85 (s, 6H), 5.41 (s, 1H), 6.33 (s, 1H), 6.75 (d, J=8.6 Hz, 1H), 6.92 (d, J=7.1 Hz, 1H). Anal. (C16H22O5) C,H.

Workup

  1. temperaturerefluxed for 1 h
  2. filtrationThe white solid was filtered
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-bceffef822ff4d3eb7299af6ae92e24d
Source dataset
uspto-grants-1999_08
Patent number
US05936120

Reaction notes

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