Hydrochloric Acid → 4-(2-Methoxyethoxy)-3-methylbenzoic acid

HRID 713010

Reaction equation

HRID 713010 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[OH-].C([P+](CCCC)(CCCC)CCCC)CCC.Br[CH2:31][CH2:32][O:33][CH3:34].Cl>C1COCC1>[CH3:34][O:33][CH2:32][CH2:31][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 681384-Hydroxy-3-methylbenzoic acidHCID 809722-Bromoethyl methyl etherHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Product 1

HCID 585513704-(2-Methoxyethoxy)-3-methylbenzoic acidYield 6.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-hydroxy-3-methyl-benzoic acid (2.0 g, 13 mmol) in THF (24 mL) was added tetrabutylphosphonium hydroxide (18 mL of 40% w/v, 26 mmol). The reaction mixture was cooled to 0° C. and then 1-bromo-2-methoxy-ethane (1.8 g, 1.2 mL, 13 mmol) was added. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was acidified using 1M HCl and the aqueous layer was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated in vacuo to yield 4-(2-methoxyethoxy)-3-methylbenzoic acid (182 mg, 6%). ESI-MS m/z calc. 210.2. found 209.2 (M-H)−; Retention time: 0.96 minutes (3 min run).

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce1380b974c74493b1c2bcf337f5aad9
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Linked notes

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