Hydrochloric Acid → HCID 68290868, compound

HRID 72949Notes

Reaction equation

HRID 72949 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]1[CH2:16][O:15][CH2:14]1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]1[CH2:14][O:15][CH2:16]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68290898Methyl 3-methyl-4-(oxetan-3-yloxy)benzoate

Product 1

HCID 68290868HCID 68290868, compound

Procedure

To methyl 4-hydroxy-3-methyl-benzoate (498 mg, 3 mmol) was added DMF (3 mL) and sodium hydride (240 mg, 6.0 mmol) followed by oxetan-3-ol (445 mg, 6 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The reaction was cooled and quenched with brine solution and extracted with EtOAc (3×10 mL). The organic layer was separated and dried over sodium sulfate and evaporated to give methyl 3-methyl-4-(oxetan-3-yloxy)benzoate. To methyl 3-methyl-4-(oxetan-3-yloxy)benzoate was added sodium hydroxide (3 mL of 1 M NaOH, 3 mmol) solution and the reaction mixture was stirred for 1 hour. The reaction was acidified with 1 M HCl solution to pH 3 and extracted with EtOAc. The organics were separated and dried and concentrated in vacuo to give 3-methyl-4-(oxetan-3-yloxy)benzoic acid. ESI-MS m/z calc. 208.1. Found 209.3 (M+1)+; Retention time: 1.04 minutes (3 min run).

Workup

  1. extractionextracted with EtOAc
  2. customThe organics were separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9563f38b6f60404ca477fdf34bc50a26
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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