Benzoic Acid → HCID 53873217, compound

HRID 1580729Notes

Reaction equation

HRID 1580729 reaction equation
C[O:2][C:3](=[O:11])C1C=CC=CC=1S.[C:12](O)(=O)[C:13]1[CH:18]=[CH:17]C=C[CH:14]=1.BrC1C=CC=CC=1.[C:28]1([O:34][CH3:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:36][CH:37]([O:42]C1C=CC(SC)=CC=1)[CH:38]=CCC.C(C1C=CC=CC=1)C.[N+](C1C=CC=CC=1)([O-])=O>ClC1C=CC=CC=1>[CH:37]([O:42][CH2:17][CH2:18][C:13]([CH3:12])=[CH:14][CH2:35][O:34][C:28]1[CH:33]=[CH:32][C:31]2[O:2][CH2:3][O:11][C:30]=2[CH:29]=1)([CH3:36])[CH3:38]

Participants

9

Reactant 7

HCID 243Benzoic AcidHCID 7416NitrobenzeneHCID 7500EthylbenzeneHCID 7519AnisoleHCID 7961BromobenzeneHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 54289734HCID 54289734, compound

Product 1

HCID 53873217HCID 53873217, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In analogous manner as described in Example 24, but using the starting compounds of formula III indicated in the following Table, the following compounds of general formula I are obtained:Ex. Empirical Molecu- Analysis % Starting com- formula lar nD20 Calc. pound of for- weight Found mula III C H Br Cl N S__________________________________________________________________________25 2-(5-Isopropoxy-3- methyl-2-pentenylthio)- C17H24O3S 308.4 1.5492 66.2 7.8 -- -- -- 10.4 2-Mercapto- benzoicacid-methylester 66.9 7.9 -- -- -- 10.4 benzoic- acid methylester26 3-(5-Isopropoxy-3-methyl- C15H21BrO2 313.2 1.5138 57.5 6.8 25.5 -- -- -- 3-Bromo- 2-pentenyloxy)-bromobenzol 58.1 7.0 25.1 -- -- -- phenol27 4-(5-Isopropoxy-3-methyl- C15H21ClOS 284.8 1.5332 63.3 7.4 -- 12.4 -- 11.3 4-Chloro- 2-pentenylthio)-chlorobenzol 63.1 7.6 -- 13.0 -- 10.6 phenol28 4-(5-Isopropoxy-3-methyl- C16H24O3 264.4 1.5050 72.7 9.2 -- -- -- -- 4-Methoxy- 2-pentenyloxy)-anisole 72.3 9.5 -- -- -- -- phenol29 4-(5-Isopropoxy-3-methyl- C16H24O2S 280.4 1.5329 68.5 8.6 -- -- -- 11.4 4-(Methyl- 2-pentenyloxy)-thioanisole 68.0 8.6 -- -- -- 10.9 thio)-phenol30 4-(5-Isopropoxy-3-methyl-2- C17H26O2 262.4 1.4992 77.8 10.0 -- -- -- -- 4-entyl- pentenyloxy)-ethylbenzol 77.5 10.7 -- -- -- -- phenol31 4-(5-Isopropoxy-3-methyl-2- C15H21NO4 279.3 1.5335 64.5 7.6 -- -- 5.0 -- 4-Nitro- pentenyloxy)-nitrobenzol 64.4 7.7 -- -- 4.8 -- phenol32 4-(5-Isopropoxy-3-methyl-2- 59.4 6.6 -- 23.4 -- -- 2,4-Dichloro- pentenyloxy)-1,3-dichloro- C15H20Cl2O2 303.2 1.5244 59.4 6.6 -- 23.6 -- -- phenol benzol__________________________________________________________________________

Workup

  1. customthe following compounds of general formula I are obtained

Sources & evidence

ORD record
ord-8855edc97d4e467a91cd292f878c4463
Source dataset
uspto-grants-1976_01
Patent number
US03933804

Reaction notes

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