Reaction SMILES: [H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:19]2[N:18]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:26]=[C:27]([CH:102]=[C:103]([O:123][CH2:124][CH2:125][CH2:126][CH2:127][N:128]4[C:140]5[CH:139]=[CH:138][CH:137]=[CH:136][C:135]=5[C:134]5[C:129]4=[CH:130][CH:131]=[CH:132][CH:133]=5)[C:104]=3[O:105][CH2:106][CH2:107][CH2:108][CH2:109][N:110]3[C:122]4[CH:121]=[CH:120][CH:119]=[CH:118][C:117]=4[C:116]4[C:111]3=[CH:112][CH:113]=[CH:114][CH:115]=4)[CH2:28][O:29][C:30]3[CH:31]=[C:32]([CH:37]=[C:38]([O:40][CH2:41][C:42]4[CH:47]=[C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][N:53]5[C:65]6[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=6[C:59]6[C:54]5=[CH:55][CH:56]=[CH:57][CH:58]=6)[C:45]([O:66][CH2:67][CH2:68][CH2:69][CH2:70][N:71]5[C:83]6[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=6[C:77]6[C:72]5=[CH:73][CH:74]=[CH:75][CH:76]=6)=[C:44]([O:84][CH2:85][CH2:86][CH2:87][CH2:88][N:89]5[C:101]6[CH:100]=[CH:99][CH:98]=[CH:97][C:96]=6[C:95]6[C:90]5=[CH:91][CH:92]=[CH:93][CH:94]=6)[CH:43]=4)[CH:39]=3)[C:33](OC)=[O:34])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>C1COCC1>[CH:55]1[C:54]2[N:53]([CH2:52][CH2:51][CH2:50][CH2:49][O:48][C:46]3[CH:47]=[C:42]([CH:43]=[C:44]([O:84][CH2:85][CH2:86][CH2:87][CH2:88][N:89]4[C:90]5[CH:91]=[CH:92][CH:93]=[CH:94][C:95]=5[C:96]5[C:101]4=[CH:100][CH:99]=[CH:98][CH:97]=5)[C:45]=3[O:66][CH2:67][CH2:68][CH2:69][CH2:70][N:71]3[C:83]4[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=4[C:77]4[C:72]3=[CH:73][CH:74]=[CH:75][CH:76]=4)[CH2:41][O:40][C:38]3[CH:37]=[C:32]([CH2:33][OH:34])[CH:31]=[C:30]([O:29][CH2:28][C:27]4[CH:26]=[C:25]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][N:18]5[C:17]6[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=6[C:11]6[C:19]5=[CH:7][CH:8]=[CH:9][CH:10]=6)[C:104]([O:105][CH2:106][CH2:107][CH2:108][CH2:109][N:110]5[C:122]6[CH:121]=[CH:120][CH:119]=[CH:118][C:117]=6[C:116]6[C:111]5=[CH:112][CH:113]=[CH:114][CH:115]=6)=[C:103]([O:123][CH2:124][CH2:125][CH2:126][CH2:127][N:128]5[C:129]6[CH:130]=[CH:131][CH:132]=[CH:133][C:134]=6[C:135]6[C:140]5=[CH:139][CH:138]=[CH:137][CH:136]=6)[CH:102]=4)[CH:39]=3)[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]=2[CH:58]=[CH:57][CH:56]=1
Reactant: COC(=O)c1cc(OCc2cc(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c2)cc(OCc2cc(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c2)c1
Agent: [Al+3]
Agent: [H-]
Agent: [Li+]
Solvent: C1CCOC1
Product: OCc1cc(OCc2cc(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c2)cc(OCc2cc(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c(OCCCCn3c4ccccc4c4ccccc43)c2)c1
Yield: 142.3 %

Procedure:
An oven-dried, magnetically stirred, 100 mL RBF was charged with a solution of LiAlH4 (9 mg, 0.141 mmol) in 40 mL freshly distilled THF. Then, a THF solution of compound 13 (0.17 g, 0.0564 mmol) was added dropwise over 0.5 hours. After stirring the reaction mixture for 2 hours at 80° C., 1 N NaOH was slowly added. The organic phase was separated and extracted with chloroform. The organics were then dried over Na2SO4 and filtered. The solvent was evaporated to give the crude product. The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:ethyl acetate=1:50 v/v) to yield 0.14 g (76%) of (3,5-bis(3,4,5-tris(4-(9H-carbazol-9-yl)butoxy)benzyloxy)phenyl)methanol (Compound 14).