Methyl 4-(benzyloxy)-3-chloro-5-isopropoxybenzoate → Methyl 3-chloro-4-hydroxy-5-isopropoxybenzoate

HRID 62744Notes

Reaction equation

HRID 62744 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[Cl:23])C1C=CC=CC=1>CO.C(Cl)Cl.CC(O)=O.[Pd]>[Cl:23][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([O:19][CH:20]([CH3:22])[CH3:21])[C:9]=1[OH:8])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 1

HCID 67041754Methyl 4-(benzyloxy)-3-chloro-5-isopropoxybenzoate

Product 1

HCID 67041588Methyl 3-chloro-4-hydroxy-5-isopropoxybenzoateYield 92.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-(benzyloxy)-3-chloro-5-isopropoxybenzoate (2) (3.00 g, 8.96 mmol) was dissolved in a mixture of MeOH (100 mL), DCM (10 mL) and AcOH (0.1 mL) and the solution was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 25° C. under H2 (full H2 mode). The solvents were removed in vacuo to afford methyl 3-chloro-4-hydroxy-5-isopropoxybenzoate (3) (2.03 g, 89%): m/z 245 [M+H]+ (ES+), 243 [M−H](ES−).

Workup

  1. customat 25° C.
  2. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f5db253460074a979603560ee7beaf1e
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

Loading…