Sodium Hydroxide → 4-Benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid

HRID 1643583Notes

Reaction equation

HRID 1643583 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[CH2:11][C:12]([CH3:15])([CH3:14])[O:13][C:9]=2[CH:8]=1)=[O:6]>CO>[CH2:19]([O:18][C:16]1[C:10]2[CH2:11][C:12]([CH3:15])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:17]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59559917HCID 59559917, compound

Product 1

HCID 595600094-Benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

NaOH (23 mL, 69 mmol, 3N aqueous solution) was added to a solution of 4-benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (77a) (7.18 g, 23 mmol) in MeOH (80 mL). The reaction mixture was heated to 60° C. for 3 hr, and concentrated in vacuo. The residue was diluted with H2O (100 mL) and washed with EtOAc (100 mL). The aqueous phase was acidified with 3N aqueous HCl to Ph ˜2 to form a white precipitate, which was filtered and dried to give a white solid (6.05 g, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.88 (s, 1 H) 7.38-7.48 (m, 4 H) 7.33 (t, J=7.07 Hz, 1 H) 7.14 (s, 1 H) 6.88 (s, 1H) 5.17 (s, 2 H) 2.98 (s, 2 H) 1.42 (s, 6 H); LCMS for C18H18O5 m/z 299.10 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with H2O (100 mL)
  3. washwashed with EtOAc (100 mL)
  4. customto form a white precipitate, which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-3077b63298354badbd23dd7cb1349a02
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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