Methanol → 2-[(4-Bromobenzyl)oxy]4-methylpentanoic acid

HRID 1744067Notes

Reaction equation

HRID 1744067 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][CH:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.CO.O1CCCC1.[Li]>O.Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][CH:8]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:9]([OH:11])=[O:10])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 22235862Methyl 2-[(4-bromobenzyl)oxy]-4-methylpentanoate

Product 1

HCID 222357912-[(4-Bromobenzyl)oxy]4-methylpentanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Methyl 2-[(4-bromobenzyl)oxy]-4-methylpentanoate in a mixture of water (3 mL), methanol (3 mL) and tetrahydrofuran (6 mL) was treated with lithium hydroxyde monohydrate (560 mg, 13.3 mmoles) until disappearance of the starting material was observed by TLC. The reaction was diluted with 1.2 N hydrochloric acid until pH 1. The aqueous phase was extracted 3 times with dichloromethane. The organic phase was concentrated under reduced pressure to afford 2-[(4-bromobenzyl)oxy]-4-methylpentanoic acid which was used as such in the next reaction.

Workup

  1. extractionThe aqueous phase was extracted 3 times with dichloromethane
  2. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70d0c30ad98e4f7eb93a3e68c70db2bf
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…