Hydrochloric Acid → HCID 12339646, compound

HRID 1985060Notes

Reaction equation

HRID 1985060 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]#N)C.[OH-:17].[K+].CCO.[OH2:22].Cl>C([O-])([O-])=O.[Na+].[Na+]>[C:4]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:22])=[O:17])([OH:3])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13462458Ethyl ((2-cyanobenzyl)oxy)acetateHCID 19096565Water ethanol

Product 1

HCID 12339646HCID 12339646, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2-cyano-benzyloxy)-acetic acid ethyl ester (J. Org. Chem. 1985, 50, 2128) (30 g, 136 mmol) and KOH (38 g, 680 mmol) in 1:1 EtOH/H2O (270 ml) was heated to 90° C. (oil bath) for 15 h. After cooling to room temperature the mixture was treated with conc. HCl until the pH=1 and extracted with CH2Cl2. The combined organic layers were dried concentrated in vacuo to yield an orange oil. The oil was dissolved in aq. Na2CO3, treated with activated carbon, filtered and the pH adjusted to 1 with conc. HCl. The resulting solid was collected by filtration and dried to yield 8.2 g of 2-[(carboxymethoxy)methyl]benzoic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 12.9 (bs, 1 H), 7.87 (dd, J=7.77, 1.14 Hz, 1 H), 7.66 (m, 1 H), 7.59 (m, 1 H), 7.39 (m, 1 H), 4.90 (s, 2 H), 4.15 (m, 2 H).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. concentrationconcentrated in vacuo
  5. customto yield an orange oil
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. filtrationThe resulting solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-791ff6d4184b4a1784d3e808fed8efce
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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