Sodium Hydroxide → 2-(Trityloxy)acetic acid

HRID 1776553Notes

Reaction equation

HRID 1776553 reaction equation
[C:1]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[C:1]([O:20][CH2:21][C:22]([OH:24])=[O:23])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12230788trityloxy-acetic Acid Ethyl Ester

Product 1

HCID 122307892-(Trityloxy)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 2-(trityloxy)acetate (8.2 g, 23.67 mmol) in EtOH (350 ml), NaOH 6M (7.89 ml, 47.3 mmol) was added at RT. The suspension slowly turned into a solution. After 1 hour, EtOH was removed under vacuum and the remaining crude was partitioned between HCl 2N and DCM. The organic phase was separated, dried over Na2SO4 and evaporated under vacuum. 2-(Trityloxy)acetic acid was obtained (7.42 g, 23.31 mmol, 98% yield) and used as such in the following reaction without further purification.

Workup

  1. additionwas added at RT
  2. customEtOH was removed under vacuum
  3. customthe remaining crude was partitioned between HCl 2N and DCM
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-8e8d09d36dca45df939420a15eb2e458
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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