Potassium Hydroxide → HCID 58236465, compound

HRID 1182811Notes

Reaction equation

HRID 1182811 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-e1d8f71efae245be86d3c545c1105c0e
Source dataset
uspto-grants-2014_03
Patent number
US08664218B2

Reaction notes

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