Hydrochloric Acid → 2-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

HRID 1920447Notes

Reaction equation

HRID 1920447 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10]/[C:9]/2=[CH:16]\[O:17][Si](C(C)C)(C(C)C)C(C)C)=[CH:4][CH:3]=1.ClC1C=CC(C2(O)CCC(C)(C)C/C/2=C\O[Si](C)(C)C)=CC=1.[Si](O/C=C1/C(C2C=CC(Cl)=CC=2)(O)CCC(C)(C)C/1)(C(C)(C)C)(C)C.Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[CH:16]=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 67079181(2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-1-(4-chlorophenyl)-4,4-dimethylcyclohexanolHCID 67079716(2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanolHCID 67079763(2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanol

Product 1

HCID 445943302-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

Procedure

reacting ((2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanol, (2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanol, or (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-1-(4-chlorophenyl)-4,4-dimethylcyclohexanol and hydrochloric acid at about 5° C. to about 20° C. to provide 2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-ene-1-carbaldehyde and isolating or not isolating the 2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-ene-1-carbaldehyde;

Workup

  1. customat about 5° C. to about 20° C.

Sources & evidence

ORD record
ord-41bf26bdeebf4a28ad00dd4336a5eb31
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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