Hydrochloric Acid → 4-(Carboxymethyl)benzoic Acid
Reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)#N.Cl.[OH-:14].[Na+].[OH2:16]>>[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([OH:16])=[O:14]Participants
5
Conditions
- Temperature
- 25 °C
Procedure
A solution of 4-cyanomethyl-benzoic acid (0.53 g, 3.31 mmol) in a 50% aqueous hydrochloric acid solution (42.8 mL) was heated at 80° C. for 16 h. At this time, the reaction was cooled to 25° C. and adjusted to pH=3 by the dropwise addition of a 50% aqueous sodium hydroxide solution. The resulting mixture was diluted with water and extracted with butanol (2×50 mL). The combined organic layers were then extracted with water (5×50 mL, pH=6–7). The aqueous extracts were adjusted to pH=3 with a 3M aqueous hydrochloric acid solution and concentrated in vacuo to afford 4-carboxymethyl-benzoic acid (70 mg, 11.7%) as a white solid: mp 235–237° C.; EI-HRMS m/e calcd for C9H8O4 (M+) 180.0422, found 180.
Workup
- extractionextracted with butanol (2×50 mL)
- extractionThe combined organic layers were then extracted with water (5×50 mL, pH=6–7)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8f31a963a9054d8fa32dcbf674524328
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223868B2
Reaction notes
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