Hydrochloric Acid → Benzoic acid, 2-(carboxymethoxy)-

HRID 2169752Notes

Reaction equation

HRID 2169752 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C:12]([O:14]C)=[O:13].[OH-].[Na+].Cl>>[C:12]([CH2:11][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:16])=[O:2])([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11287524Methyl 2-(2-methoxy-2-oxoethoxy)benzoate

Product 1

HCID 69461Benzoic acid, 2-(carboxymethoxy)-Yield 78.2%

Conditions

Temperature
80 °C

Procedure

2-Methoxycarbonylmethoxybenzoic acid methyl ester 1 (95 g, 424 mmol) was added to a 10% aqueous NaOH solution (475 ml) and heated at 80° C. for 4 hrs. The reaction mixture was cooled to room temperature and pH adjusted to 2 with dilute HCl. Crude 91 was purified by dissolving in 10% aqueous NaOH and precipitated by acidifying with HCl, to get pure 91 (65 g, 78.2%) as a white powder. M.p: 189-192° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customCrude 91 was purified
  3. dissolutionby dissolving in 10% aqueous NaOH
  4. customprecipitated

Sources & evidence

ORD record
ord-5886d926d7164a97bc2313e0352d5d13
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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