Trityl chloride → Triethylammonium 2-triphenylmethoxyimino-2-phenylacetate

HRID 435990Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[C:20]1([C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)Cl)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:1][N:2]=[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([O-:6])=[O:5])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1.[CH2:13]([NH+:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14]

Participants

Reactant 3

HCID 6456Trityl chloride

HCID 8471Triethylamine

HCID 68167312-Hydroxyimino-2-phenylacetic acid

Product 1

HCID 73676607Triethylammonium 2-triphenylmethoxyimino-2-phenylacetateYield 84%

Procedure

2-Hydroxyimino-2-phenylacetic acid (syn isomer) (4.13 g, 25.0 mmole), triethylamine (8.7 ml, 62.5 mmole) and triphenylchloromethane (10.40 g, 37.5 mmole) were reacted together as described in Preparation 2(a) to give triethylammonium 2-triphenylmethoxyimino-2-phenylacetate (syn isomer) as a white solid (10.625 g, 21 mmole, 84%) m.p. 166 to 175 (dec), λmax 260 nm, inflexions at 264 and 292 nm (ε15,000; 14,400 and 2,300 respectively).

Sources & evidence

ORD record: ord-17f96ff723874c17a709ad9c17475609
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04007174

Reaction notes

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