Sodium Hydroxide → HCID 19027302, compound

HRID 2256776Notes

Reaction equation

HRID 2256776 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH:2]=C.[CH2:20]([O:23]CCOCCOC1C=CC(C(OC)=O)=CC=1)[CH:21]=[CH2:22].[OH-].[Na+]>CO>[CH2:20]([O:23][CH2:2][CH2:1][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 190272884-(2-{2-[(Prop-2-en-1-yl)oxy]ethoxy}ethoxy)benzoic acidHCID 19027301Methyl 4-(2-{2-[(prop-2-en-1-yl)oxy]ethoxy}ethoxy)benzoate

Product 1

HCID 19027302HCID 19027302, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

These compounds were synthesized by similar methods. The representative synthesis of 4-(2-(2-allyloxyethoxy)ethoxy)benzoic acid (11) is presented. A mixture of 8.39 grams (0.03 mole) of the obtained methyl 4-(2-(2-allyloxy-ethoxy)ethoxy)benzoate (7), 6 ml of 50% aqueous sodium hydroxide solution and 150 ml of methanol was stirred under reflux for three hours. Methanol was distilled off (100 ml) and water 600 ml was added. The reaction mixture was acidified with hydrochloric acid. After cooling to 0° C., a white solid was filtered and set aside. The filtrate was extracted with dichloromethane and the extracted material was evaporated to a white solid which was combined with the set-aside material. The combined material was dried under vacuum to yield 4.4 g of product (94.3%). 1H-NMR (CDCl3, TMS): d=3.81-4.25 (m, 10H, --CH2 --(OCH2CH2)2 -- ), 5.23 and 5.9 (m, 3H, CH2 =CH--), 6.95 and 8.05 (2d, 4 aromatic protons), 12.2 (s, 1H, --COOH).

Workup

  1. customThese compounds were synthesized by similar methods
  2. temperatureunder reflux for three hours
  3. distillationMethanol was distilled off (100 ml) and water 600 ml
  4. additionwas added
  5. filtrationa white solid was filtered
  6. extractionThe filtrate was extracted with dichloromethane
  7. customthe extracted material was evaporated to a white solid which
  8. customThe combined material was dried under vacuum

Sources & evidence

ORD record
ord-3ac563d5d9934382807ed3baa13b2fd9
Source dataset
uspto-grants-1997_08
Patent number
US05656197

Reaction notes

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