Sodium Hydroxide → 4-[(Oxan-4-yl)oxy]benzoic acid

HRID 452866Notes

Reaction equation

HRID 452866 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[O:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 65018987HCID 65018987, compound

Product 1

HCID 242295194-[(Oxan-4-yl)oxy]benzoic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 4-(tetrahydro-2H-pyran-4-yloxy)benzoate (D5) (0.73 g) in EtOH (10 ml) was treated with 1M NaOH (5.84 ml) and the mixture stirred at 60° C. for 5 h. The solution was cooled to rt and the EtOH was evaporated. The aqueous was washed with DCM (2×10 ml) and acidified. The solid was filtered off, washed with water and dried to give the title compound (D6) (0.55 g). MS electrospray (−ion) 221 (M-H). 1H NMR δ (DMSO-d6): 7.87 (2H, d, J=8.5 Hz), 7.05 (2H, d, J=8.5 Hz), 4.69 (1H, m), 3.85 (2H, m), 3.50 (2H, m), 1.98 (2H, m), 1.59 (2H, m).

Workup

  1. temperatureThe solution was cooled to rt
  2. customthe EtOH was evaporated
  3. washThe aqueous was washed with DCM (2×10 ml)
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5697eb0d72e9468b97ace0ec1bc98f25
Source dataset
uspto-grants-2013_07
Patent number
US08492375B2

Reaction notes

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