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Dimethylformamide → 2,4-Bis-benzyloxy-5-isopropyl-benzoyl chloride

HRID 425182
Notes
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Reaction equation

HRID 425182 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([CH:26]([CH3:28])[CH3:27])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:32])=O.CN(C=O)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([CH:26]([CH3:28])[CH3:27])=[CH:14][C:10]=1[C:11]([Cl:32])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 591678792,4-Dibenzyloxy-5-isopropyl-benzoic acid

Product 1

HCID 592631702,4-Bis-benzyloxy-5-isopropyl-benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Bis-benzyloxy-5-isoproyl-benzoic acid (0.2 g, 0.53 mmol) was dissolved in DCM (10 ml) and treated with oxalyl chloride (1.5 g, 12 mmol) and a catalytic amount of DMF. Stir reaction mixture at room temperature for 14 hours. Solvent was removed in vacuo. The crude material was dissolved in toluene and evaporated. Crude 2,4-bis-benzyloxy-5-isopropyl-benzoyl chloride was obtained as oil (200 mg).

Workup

  1. customreaction mixture at room temperature for 14 hours
  2. customSolvent was removed in vacuo
  3. dissolutionThe crude material was dissolved in toluene
  4. customevaporated

Sources & evidence

ORD record
ord-51e5ceb0b9344b82af027f35dde22495
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106057B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes