Sodium borohydride → 2-Methoxy-4-[3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy]benzyl alcohol

HRID 537616Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]2[CH2:18][CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:15]([O:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH2:14]2)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[BH4-].[Na+]>C(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]2[CH2:18][CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:15]([O:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH2:14]2)[CH:8]=[CH:7][C:4]=1[CH2:5][OH:6]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Methoxy-4-[3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy]benzaldehyde (272 mg, 0.26 mmol) was suspended in chloroform-methanol (6 ml+0.5 ml), and sodium borohydride (29 mg, 0.77 mmol) was added. After stirring at 60° C. overnight, the mixture was dissolved in chloroform (12 ml), and washed with 0.5N hydrochloric acid (8 ml) and pure water (8 ml). The solvent was evaporated, and the residue was precipitated with acetonitrile (2.5 ml) to give 2-methoxy-4-[3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy]benzyl alcohol (260 mg, 0.25 mmol, 95%).

Workup

washwashed with 0.5N hydrochloric acid (8 ml) and pure water (8 ml)
customThe solvent was evaporated
customthe residue was precipitated with acetonitrile (2.5 ml)

Sources & evidence

ORD record: ord-f464ef4eec624d8faf7d07a5ccff2f15
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859732B2

Reaction notes

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