Benzoxazole → 2-(4-Methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzene

HRID 1528558Notes

Reaction equation

HRID 1528558 reaction equation
O1C2C=CC=CC=2N=C1.NC1C(O)=CC=CC=1C.C(OC1C=C(CO)C(OCCCCCC)=CC=1C=O)CCCCC.NC1C=C(C(C)(C)C)C=CC=1O.[CH3:55][C:56]1[C:61]2[N:62]=[C:63]([C:65]3[C:72]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79])=[CH:71][C:68]([CH:69]=[O:70])=[C:67]([O:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])[CH:66]=3)[O:64][C:60]=2[CH:59]=[CH:58][CH:57]=1>>[CH3:55][C:56]1[C:61]2[N:62]=[C:63]([C:65]3[CH:66]=[C:67]([O:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])[C:68]([CH2:69][OH:70])=[CH:71][C:72]=3[O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79])[O:64][C:60]=2[CH:59]=[CH:58][CH:57]=1

Participants

6

Reactant 5

HCID 9228Benzoxazole2×HCID 709822-Amino-4-tert-butylphenolHCID 30141382-Amino-m-cresolHCID 867124922,5-Bis(hexyloxy)-4-(hydroxymethyl)benzaldehydeHCID 900059844-(4-Methylbenzoxazolyl)-2,5-bis(hexyloxy)benzaldehyde

Product 1

HCID 867124912-(4-Methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzeneYield 71%

Procedure

The sensor Zinhbo-5 can be synthesized as shown in Scheme 1, which requires a sequential construction of two benzoxazole units. The first benzoxazole unit is constructed by reaction of 2-amino-m-cresol with 2,5-bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde in three steps (in 71% yield). The second benzoxazole unit is synthesized by reaction of 2-amino-4-(tert-butyl)phenol with 4-(4-methylbenzoxazolyl)-2,5-bis(hexyloxy)benzaldehyde.

Workup

  1. customThe sensor Zinhbo-5 can be synthesized

Sources & evidence

ORD record
ord-8330dbbe449f465ea4cac4a869e01603
Source dataset
uspto-grants-2015_07
Patent number
US09090602B2

Reaction notes

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