4-Hydroxybenzaldehyde → HCID 86749099, compound

HRID 128790Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10]/[C:11](=[CH:14]\[CH2:15][C:16]1[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]=1[CH3:24])/[CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[CH3:12]/[C:11](=[CH:14]\[CH2:15][C:16]1[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]=1[CH3:24])/[CH2:10][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 1264-Hydroxybenzaldehyde

HCID 11776Triphenylphosphine

HCID 220568ethyl N-ethoxycarbonyliminocarbamate

HCID 5369482HCID 5369482, compound

Product 1

HCID 86749099HCID 86749099, compoundYield 51.8%

Procedure

By the method of example 13 above, 4-hydroxybenzaldehyde (12.0 g) and (2E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenol (Chem. Abstr., 94, 65904h) (20.5 g) are coupled with triphenylphosphine and diethyl azodicarboxylate to provide 4-((2E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenyloxy)benzaldehyde (15.9 g, 50%) as a colorless oil after chromatography. By the method of example 2 above, this is converted into the title compound, mp 136°-137° after recrystallization from hexane-dichloromethane.

Sources & evidence

ORD record: ord-493ab340e43f44d28e3ab8e00cbc7d7b
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464865

Reaction notes

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