Potassium Hydroxide → HCID 58236465, compound

HRID 389969Notes

Reaction equation

HRID 389969 reaction equation
[OH-].[K+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([O:11]C)=[O:10]>CO.O>[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58236468Methyl 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoate

Product 1

HCID 58236465HCID 58236465, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous potassium hydroxide (50% w/v, 1.0 ml) was added to a mixture of methyl 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoate (560 mg, 1.88 mmol) in methanol (12 ml) and water (4 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue diluted with water (20 ml) and acidified by the addition of 2M hydrochloric acid (10 ml). The organic material was extracted with dichloromethane (2×20 ml) and the combined organic extracts were evaporated in vacuo. The residue was triturated with a mixture of petroleum ether and diethyl ether to afford 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoic acid (392 mg, 73%) as a colourless solid. 1H NMR (DMSO-d6) 12.38 (1H, br s), 7.59 (1H, s), 6.84 (1H, s), 5.31 (2H, s), 5.20 (2H, s), 3.41 (6H, s), 3.21 (1H, m), 1.18 (6H, d). MS: [M+Na]+ 307.

Workup

  1. temperatureat reflux for 3 hours
  2. customwas removed in vacuo
  3. additionthe residue diluted with water (20 ml)
  4. additionacidified by the addition of 2M hydrochloric acid (10 ml)
  5. extractionThe organic material was extracted with dichloromethane (2×20 ml)
  6. customthe combined organic extracts were evaporated in vacuo
  7. customThe residue was triturated with a mixture of petroleum ether and diethyl ether

Sources & evidence

ORD record
ord-805a77f037e242558b0a627f57cdf596
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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