Hydrochloric Acid → 4-Chloro-3,5-diisopropoxybenzoic acid

HRID 62751Notes

Reaction equation

HRID 62751 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[O:16][CH:17]([CH3:19])[CH3:18].[OH-].[Na+].Cl>>[Cl:1][C:2]1[C:11]([O:12][CH:13]([CH3:14])[CH3:15])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:16][CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67041833Methyl 4-chloro-3,5-diisopropoxybenzoate

Product 1

HCID 670418114-Chloro-3,5-diisopropoxybenzoic acidYield 68.8%

Conditions

Temperature
100 °C

Procedure

Methyl 4-chloro-3,5-diisopropoxybenzoate (5) (93 mg, 0.32 mmol) was suspended in 2M sodium hydroxide (1.6 mL, 3.2 mmol) and stirred at 100° C. for 3 h. After cooling to RT the mixture was acidified by the addition of 1 M HCl. The resulting precipitate was collected by filtration and dried in vacuo to afford 4-chloro-3,5-diisopropoxybenzoic acid (6) (60 mg, 66% yield) as a white solid. This material was used in the subsequent reaction step without purification.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9c3a79757fb14569bc674a86fcea72ca
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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