Hydrochloric Acid → 2-(3-Bromobenzyloxy)ethanol

HRID 1021160Notes

Reaction equation

HRID 1021160 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-ef7c7d306204474787bef04d9ea2bd32
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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