Hydrochloric Acid → 3-Chloro-4-propoxybenzoic acid

HRID 423353Notes

Reaction equation

HRID 423353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH3:15])[C:5]([O:7]C)=[O:6].Cl.CCOC(C)=O>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH3:15])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 52457502Methyl 3-chloro-4-(propyloxy)benzoate

Product 1

HCID 87071503-Chloro-4-propoxybenzoic acidYield 67.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 3-chloro-4-(propyloxy)benzoate (D99) (12.22 g, 0.053 mol) in ethanol (40 ml) and 2M NaOH aq. (40 ml) was heated at 60° C. for 3 hours. The reaction was allowed to cool and then left at room temperature over the weekend. The reaction mixture was poured into a mixture of dilute aq. HCl and EtOAc. The organic layer was separated, dried and evaporated to give a solid which was triturated with ether to give the title compound as a white solid (7.7 g). δH (400 MHz, d6-DMSO) 1.00 (3H, t), 1.67-1.87 (2H, m) 4.10 (2H, t), 7.24 (1H, d), 7.84-8.06 (2H, m), 12.97 (1H, br s). MS (ES) C10H1135ClO3 requires 214; found 213 (M−H+).

Workup

  1. temperatureto cool
  2. waitleft at room temperature over the weekend
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated
  6. customto give a solid which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-153a2f1728044f5a883024db28d1eb05
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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