Hydrochloric Acid → 2-(3-Bromobenzyloxy)ethanol

HRID 2172823Notes

Reaction equation

HRID 2172823 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)[CH:14]=[CH:15][CH:16]=1.Cl>CCCCCCC>[Br:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH2:17][O:18][CH2:19][CH2:20][OH:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 873062-(3-Bromophenyl)-1,3-dioxolane

Product 1

HCID 579568182-(3-Bromobenzyloxy)ethanol

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A solution of DIBAL-H in heptane is added under an inert atmosphere to a cooled (−78° C.) solution of 2-(3-bromophenyl)-1,3-dioxolane in hexanes. The reaction mixture is stirred until no starting material is seen by TLC. Aqueous HCl (1N) is added to the reaction mixture while warming to room temperature. The product is extracted with EtOAc. Combined organic layers are dried over anhydrous MgSO4, and concentrated under reduced pressure to give 2-(3-bromobenzyloxy)ethanol.

Workup

  1. extractionThe product is extracted with EtOAc
  2. dry with materialCombined organic layers are dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e506ac544616480a8c4c6249bbdc225c
Source dataset
uspto-grants-2015_06
Patent number
US09056849B2

Reaction notes

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