Dimethylformamide → 4-Formylbenzoic acid

HRID 1588920Notes

Reaction equation

HRID 1588920 reaction equation
S(Cl)(Cl)=[O:2].CN(C)[CH:7]=[O:8].C(N[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(C)C.C1[CH2:24][O:23]CC1>C1C=CC=CC=1>[C:24]([C:14]1[CH:15]=[CH:16][C:17]([CH:7]=[O:8])=[CH:18][CH:19]=1)([OH:23])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 62386Cyclohexylisopropylamine

Product 1

HCID 120884-Formylbenzoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The acid chloride of 4-carboxybenzaldehyde (7.0 g, 46.5 mmol) was prepared in the same manner as in Example 29 using thionyl chloride (3.5 mL) and dimethylformamide (0.34 mL) in benzene (250 mL). The amide was prepared from the acid chloride in the same manner and using the same workup procedure as in Example 29 using N-isopropyl-N-cyclohexyl amine (13.3 g, 93.1mmol) in THF (150 mL) at 0° C. The crude product was suitable for use without further purification.

Workup

  1. customat 0° C
  2. customThe crude product was suitable for use without further purification

Sources & evidence

ORD record
ord-9136523ec8fb49fbbde5c8f8baf2c65d
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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