Hydrochloric Acid → Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoate

HRID 1982807Notes

Reaction equation

HRID 1982807 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=1)=[O:20].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:27]([OH:28])[C:24]1[CH:23]=[CH:22][C:21]([C:19]([O:18][CH3:17])=[O:20])=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 5462224Magnesium

Product 1

HCID 21909317Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoateYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was prepared from 2-benzyloxybromobenzene (5.3 g), magnesium (0.49 g) and tetrahydrofuran (160 mL). The obtained Grignard reagent was added to a solution of methyl terephthalaldehydate (3.3 g) in tetrahydrofuran (60 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water and dilute hydrochloric acid, and the mixture was extracted with ethylacetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=4/1) to give methyl 4-[(2-benzyloxyphenyl)-hydroxymethyl]benzoate (2.6 g).

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-894a099644a84e08943560c4073f4008
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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