Water → Ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylate

HRID 1596801Notes

Reaction equation

HRID 1596801 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)O)=[C:8]([CH2:21][OH:22])[CH:7]=1)=[O:5])[CH3:2].O.CCOC(C)=O>OP(O)(O)=O>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH:12]2[C:9]3[C:8](=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=3)[CH2:21][O:22]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 21703106(4-Ethoxycarbonyl-2-hydroxymethylphenyl)(4-fluorophenyl)methanol

Product 1

HCID 21703105Ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylate

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
80 °C

Procedure

Crude (4-ethoxycarbonyl-2-hydroxymethylphenyl)(4-fluorophenyl)methanol (30 g) is dissolved in H3PO4 (60%, 250 ml) and the solution is heated to 80° C. for 1.5 hours. Water (300 ml) and EtOAc (100 ml) is added and the phases are separated. The aqueous phase is further extracted with EtOAc (100 ml). The organic phases are joined and the solvents are removed in vacuo. The yield of the remaining somewhat impure oil is 30 g.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is further extracted with EtOAc (100 ml)
  3. customthe solvents are removed in vacuo

Sources & evidence

ORD record
ord-68d755d63c5e4c59aac0475f3ab96e11
Source dataset
uspto-grants-2001_09
Patent number
US06291689B1

Reaction notes

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